Skip to main content

2016 | OriginalPaper | Buchkapitel

4. Insertion of CO2 into E–X Bonds

verfasst von : Michele Aresta, Angela Dibenedetto, Eugenio Quaranta

Erschienen in: Reaction Mechanisms in Carbon Dioxide Conversion

Verlag: Springer Berlin Heidelberg

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

This chapter deals with the “insertion” reactions of carbon dioxide (CO2) into E–X bonds, where E and X represent several different (sets of) atoms, such as M–H, M–OH, M–C, M–OR, M–O2, M–N, M–P, C–C, C–N, Si–H, and M–M (M = metal). Such reactions are relevant to catalysis for the formation of new bonds in which CO2 may be implied (C–C bonds or C–E bonds) and thus to the conversion of CO2 into added-value chemicals. The insertion product can be thermodynamically and kinetically stable or labile, offering in the latter case the opportunity of a catalytic path.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Sneeden RPA (1982) Reactions of carbon dioxide. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive organometallic chemistry, vol 8. Pergamon, New York, pp 225–283 Sneeden RPA (1982) Reactions of carbon dioxide. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive organometallic chemistry, vol 8. Pergamon, New York, pp 225–283
2.
Zurück zum Zitat Eisenberg DC, Norton JR (1991) Hydrogen-atom transfer reactions of transition-metal hydrides. Isr J Chem 31:55–66 Eisenberg DC, Norton JR (1991) Hydrogen-atom transfer reactions of transition-metal hydrides. Isr J Chem 31:55–66
3.
Zurück zum Zitat Labinger JA (1992) Nucleophilic reactivity of transition metal hydrides. In: Dedieu A (ed) Transition metal hydrides, Chap 10. VCH, New York Labinger JA (1992) Nucleophilic reactivity of transition metal hydrides. In: Dedieu A (ed) Transition metal hydrides, Chap 10. VCH, New York
4.
Zurück zum Zitat Kristjanadottir SS, Norton JR (1992) Acidity of hydrido transition metal complexes in solution. In: Dedieu A (ed) Transition metal hydrides, Chap 9. VCH, New York Kristjanadottir SS, Norton JR (1992) Acidity of hydrido transition metal complexes in solution. In: Dedieu A (ed) Transition metal hydrides, Chap 9. VCH, New York
5.
Zurück zum Zitat Aresta M, Dibenedetto A, Pápai I, Schubert G, Macchioni A, Zuccaccia D (2004) Behaviour of [PdH(dppe)2]X (X = CF3SO 3 -, SbF6 -, BF4 -) as proton or hydride donor: relevance to catalysis. Chem Eur J 10:3708–3716 Aresta M, Dibenedetto A, Pápai I, Schubert G, Macchioni A, Zuccaccia D (2004) Behaviour of [PdH(dppe)2]X (X = CF3SO 3 -, SbF6 -, BF4 -) as proton or hydride donor: relevance to catalysis. Chem Eur J 10:3708–3716
6.
Zurück zum Zitat Hawackery J, Lehn J-M, Zeissel R (1984) Electrocatalytic reduction of carbon dioxide mediated by Re(dipy)(CO)3Cl. J Chem Soc Chem Commun 328–329 Hawackery J, Lehn J-M, Zeissel R (1984) Electrocatalytic reduction of carbon dioxide mediated by Re(dipy)(CO)3Cl. J Chem Soc Chem Commun 328–329
7.
Zurück zum Zitat Hawackery J, Lehn J-M, Zeissel R (1986) Photochemical and electrochemical reduction of CO2 to CO mediated by (2,2′ bipyridine)tricarbonyl-rhenium(I) and related complexes as homogeneous catalysts. Helv Chim Acta 69:1990–2012 Hawackery J, Lehn J-M, Zeissel R (1986) Photochemical and electrochemical reduction of CO2 to CO mediated by (2,2′ bipyridine)tricarbonyl-rhenium(I) and related complexes as homogeneous catalysts. Helv Chim Acta 69:1990–2012
8.
Zurück zum Zitat Bradley MG, Roberts DA, Geoffroy GL (1981) Photogeneration of reactive ReH(diphos)2. Its reversible coordination of CO2 and activation of aromatic C-H bonds. J Am Chem Soc 103:379–384 Bradley MG, Roberts DA, Geoffroy GL (1981) Photogeneration of reactive ReH(diphos)2. Its reversible coordination of CO2 and activation of aromatic C-H bonds. J Am Chem Soc 103:379–384
9.
Zurück zum Zitat Sullivan BP, Meyer TJ (1984) Photoinduced irreversible insertion of CO2 into a metal-hydride bond. J Chem Soc Chem Comm 1244–1245 Sullivan BP, Meyer TJ (1984) Photoinduced irreversible insertion of CO2 into a metal-hydride bond. J Chem Soc Chem Comm 1244–1245
10.
Zurück zum Zitat Sullivan BP, Krist K, Guard HE (1993) Formation of formate by insertion into a metal hydride bond. In: Electrochemical and electrocatalytic reactions of carbon dioxide. Elsevier, Amsterdam, pp. 128–129 Sullivan BP, Krist K, Guard HE (1993) Formation of formate by insertion into a metal hydride bond. In: Electrochemical and electrocatalytic reactions of carbon dioxide. Elsevier, Amsterdam, pp. 128–129
11.
Zurück zum Zitat Kolomnikov IS, Gusev AI, Alexandrov GG, Loboeva TS, Strutchov Yu T, Volpin MA (1973) Structure of the product formed in the reaction of carbon dioxide with ruthenium hydride complexes. J Organomet Chem 59:349–351 Kolomnikov IS, Gusev AI, Alexandrov GG, Loboeva TS, Strutchov Yu T, Volpin MA (1973) Structure of the product formed in the reaction of carbon dioxide with ruthenium hydride complexes. J Organomet Chem 59:349–351
12.
Zurück zum Zitat Darensbourg MY, Carlton EA (1987) Anionic transition metal hydrides. Adv Organomet Chem 27:1–47 Darensbourg MY, Carlton EA (1987) Anionic transition metal hydrides. Adv Organomet Chem 27:1–47
13.
Zurück zum Zitat DuBois DL, Berning DE (2000) Hydricity of transition metal hydrides and its role in CO2 reduction. Appl Organomet Chem 14(12):860–862 DuBois DL, Berning DE (2000) Hydricity of transition metal hydrides and its role in CO2 reduction. Appl Organomet Chem 14(12):860–862
14.
Zurück zum Zitat Aresta M, Dibenedetto A, Angelini A (2014) Catalysis for the valorization of exhaust carbon: from carbon dioxide to chemicals, materials and fuels. Technological use of CO2. Chem Rev 114:1709–1743 Aresta M, Dibenedetto A, Angelini A (2014) Catalysis for the valorization of exhaust carbon: from carbon dioxide to chemicals, materials and fuels. Technological use of CO2. Chem Rev 114:1709–1743
15.
Zurück zum Zitat Inoue Y, Izumida H, Sasaki Y, Hashimoto H (1976) Catalytic fixation of carbon dioxide to formic acid by transition metal complexes under mild conditions. Chem Lett 863–864 Inoue Y, Izumida H, Sasaki Y, Hashimoto H (1976) Catalytic fixation of carbon dioxide to formic acid by transition metal complexes under mild conditions. Chem Lett 863–864
16.
Zurück zum Zitat Jessop PG, Ikariya T, Noyori R (1995) Homogeneous hydrogenation of carbon dioxide. Chem Rev 95:259–272 Jessop PG, Ikariya T, Noyori R (1995) Homogeneous hydrogenation of carbon dioxide. Chem Rev 95:259–272
17.
Zurück zum Zitat Leitner W (1995) Carbon dioxide as a raw material: the synthesis of formic acid and its derivatives from CO2. Angew Chem Int Ed Engl 34:2207–2221 Leitner W (1995) Carbon dioxide as a raw material: the synthesis of formic acid and its derivatives from CO2. Angew Chem Int Ed Engl 34:2207–2221
18.
Zurück zum Zitat Jessop PG, Joo F, Tai C-C (2004) Recent advances in the homogeneous hydrogenation of carbon dioxide. Coord Chem Rev 248:2425–2442 Jessop PG, Joo F, Tai C-C (2004) Recent advances in the homogeneous hydrogenation of carbon dioxide. Coord Chem Rev 248:2425–2442
19.
Zurück zum Zitat Federsel C, Jackstell R, Beller M (2010) State-of-the-art catalysts for hydrogenation of carbon dioxide. Angew Chem Int Ed 49:6254–6257 Federsel C, Jackstell R, Beller M (2010) State-of-the-art catalysts for hydrogenation of carbon dioxide. Angew Chem Int Ed 49:6254–6257
20.
Zurück zum Zitat Leitner W, Dinjus E, Gassner F (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis concepts and applications. Wiley-VCH, Weinheim, p 486 Leitner W, Dinjus E, Gassner F (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis concepts and applications. Wiley-VCH, Weinheim, p 486
21.
Zurück zum Zitat Kovacs G, Schubert G, Joo F, Pápai I (2006) Theoretical investigation of catalytic HCO3 − hydrogenation in aqueous solutions. Catal Today 115:53–60 Kovacs G, Schubert G, Joo F, Pápai I (2006) Theoretical investigation of catalytic HCO3 hydrogenation in aqueous solutions. Catal Today 115:53–60
22.
Zurück zum Zitat Engel DC, Versteeg GF, van Swaaij WPM (1997) Chemical equilibrium of hydrogen and aqueous solutions of 1:1 bicarbonate and formate salts with a common cation. Fluid Phase Equilib 135:109–136 Engel DC, Versteeg GF, van Swaaij WPM (1997) Chemical equilibrium of hydrogen and aqueous solutions of 1:1 bicarbonate and formate salts with a common cation. Fluid Phase Equilib 135:109–136
23.
Zurück zum Zitat Moret S, Dyson P, Laurenczy G (2014) Direct synthesis of formic acid from CO2 by hydrogenation in acidic media. Nat Commun 5:1–7 Moret S, Dyson P, Laurenczy G (2014) Direct synthesis of formic acid from CO2 by hydrogenation in acidic media. Nat Commun 5:1–7
24.
Zurück zum Zitat Aresta M, Gobetto R, Quaranta E, Tommasi I (1992) A bonding-reactivity relationship for Ni(PCy3)2(CO2): a comparative solid-state-solution nuclear magnetic resonance study (31P, 13C) as a diagnostic tool to determine the mode of bonding of CO2 to a metal center. Inorg Chem 31:4286–4290 Aresta M, Gobetto R, Quaranta E, Tommasi I (1992) A bonding-reactivity relationship for Ni(PCy3)2(CO2): a comparative solid-state-solution nuclear magnetic resonance study (31P, 13C) as a diagnostic tool to determine the mode of bonding of CO2 to a metal center. Inorg Chem 31:4286–4290
25.
Zurück zum Zitat Tanaka K, Ooyama D (2002) Multi-electron reduction of CO2 via Ru-CO2 -C(O)OH, -CO, -CHO, and CH2OH species. Coord Chem Rev 226:211–218 Tanaka K, Ooyama D (2002) Multi-electron reduction of CO2 via Ru-CO2 -C(O)OH, -CO, -CHO, and CH2OH species. Coord Chem Rev 226:211–218
26.
Zurück zum Zitat DuBois DL, Miedaner AR, Curtis Haltiwanger RC (1991) Electrochemical reduction of carbon dioxide catalyzed by [Pd(triphosphine)(solvent)](BF4)2 complexes: synthetic and mechanistic studies. J Am Chem Soc 113:8753–8764 DuBois DL, Miedaner AR, Curtis Haltiwanger RC (1991) Electrochemical reduction of carbon dioxide catalyzed by [Pd(triphosphine)(solvent)](BF4)2 complexes: synthetic and mechanistic studies. J Am Chem Soc 113:8753–8764
27.
Zurück zum Zitat Ishida H, Tanaka K, Morimoto M, Tanaka T (1986) Isolation of intermediates in the water gas shift reactions catalyzed by [Ru(bpy)2(CO)Cl]+ and [Ru(bpy)2(CO)2]2+. Organometallics 5:724–730 Ishida H, Tanaka K, Morimoto M, Tanaka T (1986) Isolation of intermediates in the water gas shift reactions catalyzed by [Ru(bpy)2(CO)Cl]+ and [Ru(bpy)2(CO)2]2+. Organometallics 5:724–730
28.
Zurück zum Zitat Dubois DL (1997) Development of transition metal phosphine complexes as electrocatalysts for CO2 and CO reduction. Comments Inorg Chem 19:307–325 Dubois DL (1997) Development of transition metal phosphine complexes as electrocatalysts for CO2 and CO reduction. Comments Inorg Chem 19:307–325
29.
Zurück zum Zitat Cámpora J, Palma P, del Río D, Álvarez E (2005) CO insertion reactions into the M − OH bonds of monomeric nickel and palladium hydroxides. Reversible decarbonylation of hydroxycarbonyl palladium complex. Organometallics 23(8):1652–1655 Cámpora J, Palma P, del Río D, Álvarez E (2005) CO insertion reactions into the M − OH bonds of monomeric nickel and palladium hydroxides. Reversible decarbonylation of hydroxycarbonyl palladium complex. Organometallics 23(8):1652–1655
30.
Zurück zum Zitat Bertini I, Banci Luchinat C, Monnanni R (1987) The enzyme carbonic anhydrase. In: Aresta M, Forti G (eds) Carbon dioxide as a source of carbon: biochemical and chemical use. NATO Advanced Study Institute, Pugnochiuso Bertini I, Banci Luchinat C, Monnanni R (1987) The enzyme carbonic anhydrase. In: Aresta M, Forti G (eds) Carbon dioxide as a source of carbon: biochemical and chemical use. NATO Advanced Study Institute, Pugnochiuso
31.
Zurück zum Zitat Palmer DA, Van Eldik R (1983) The chemistry of metal carbonate and CO2 complexes. Chem Rev 83:651–731 Palmer DA, Van Eldik R (1983) The chemistry of metal carbonate and CO2 complexes. Chem Rev 83:651–731
32.
Zurück zum Zitat Zhang X, Van Eldik R, Koike T, Kimura E (1993) Kinetics and mechanism of hydration of CO2 and dehydration of HCO3 - catalyzed by a Zn(II) complex of 1,5,9-tetraazadodecane. Inorg Chem 32:5749–5755 Zhang X, Van Eldik R, Koike T, Kimura E (1993) Kinetics and mechanism of hydration of CO2 and dehydration of HCO3 - catalyzed by a Zn(II) complex of 1,5,9-tetraazadodecane. Inorg Chem 32:5749–5755
33.
Zurück zum Zitat Zhang X, Van Eldik R (1995) A functional model for carbonic anhydrase. Thermodynamic and kinetic study of a tetraazacyclododecane complex of Zn(II). Inorg Chem 34:5606–5614 Zhang X, Van Eldik R (1995) A functional model for carbonic anhydrase. Thermodynamic and kinetic study of a tetraazacyclododecane complex of Zn(II). Inorg Chem 34:5606–5614
34.
Zurück zum Zitat Huang D, Maklyents OV, Tan LL, Lee SC, Rybak-Akimova EV, Holm RH (2011) Kinetics and mechanistic study of an extremely rapid carbon dioxide fixation reaction. Proc Natl Acad Sci USA 108(4):1222–1227 Huang D, Maklyents OV, Tan LL, Lee SC, Rybak-Akimova EV, Holm RH (2011) Kinetics and mechanistic study of an extremely rapid carbon dioxide fixation reaction. Proc Natl Acad Sci USA 108(4):1222–1227
35.
Zurück zum Zitat Flynn BR, Vaska L (1973) Carbon dioxide fixation leading to stable molecular bicarbonato complexes of d8 metals. J Am Chem Soc 95:5081–5082 Flynn BR, Vaska L (1973) Carbon dioxide fixation leading to stable molecular bicarbonato complexes of d8 metals. J Am Chem Soc 95:5081–5082
36.
Zurück zum Zitat Truscott BJ, Nelson DJ, Alexandra MZ, Slawin AMZ, Nolan SP (2014) CO2 fixation employing an iridium(I)-hydroxide complex. Chem Commun 50:286–288 Truscott BJ, Nelson DJ, Alexandra MZ, Slawin AMZ, Nolan SP (2014) CO2 fixation employing an iridium(I)-hydroxide complex. Chem Commun 50:286–288
37.
Zurück zum Zitat Lohr TL, Piers WE, Parvez M (2013) Reversible insertion of carbon dioxide into Pt(II)–hydroxo bonds. Dalton Trans 42:14742–14748 Lohr TL, Piers WE, Parvez M (2013) Reversible insertion of carbon dioxide into Pt(II)–hydroxo bonds. Dalton Trans 42:14742–14748
38.
Zurück zum Zitat Aresta M, Schloss MV (eds) (1990) Enzymatic and model carboxylation and reduction reactions for carbon dioxide utilization. NATO Advanced Study Institute, Riva dei Tessali Aresta M, Schloss MV (eds) (1990) Enzymatic and model carboxylation and reduction reactions for carbon dioxide utilization. NATO Advanced Study Institute, Riva dei Tessali
39.
Zurück zum Zitat Volpin ME (1972) The reaction of organometallic compounds of transition metals with molecular nitrogen and CO2. Pure Appl Chem 30(3):607–626 Volpin ME (1972) The reaction of organometallic compounds of transition metals with molecular nitrogen and CO2. Pure Appl Chem 30(3):607–626
40.
Zurück zum Zitat Albano P, Aresta M, Manassero M (1980) Interaction of carbon dioxide with coordinatively unsaturated rhodium(I) complexes with the ligand 1,2-bis(diphenylphosphino)ethane. Inorg Chem 19:1069–1070 Albano P, Aresta M, Manassero M (1980) Interaction of carbon dioxide with coordinatively unsaturated rhodium(I) complexes with the ligand 1,2-bis(diphenylphosphino)ethane. Inorg Chem 19:1069–1070
41.
Zurück zum Zitat Allen OR, Dalgarno SJ, Field DL, Jensen P, Willis AC (2009) Insertion of CO2 into the Ru−C bonds of cis- and trans-Ru(dmpe)2Me2(dmpe=Me2PCH2CH2PMe2). Organometallics 28:2385–2390 Allen OR, Dalgarno SJ, Field DL, Jensen P, Willis AC (2009) Insertion of CO2 into the Ru−C bonds of cis- and trans-Ru(dmpe)2Me2(dmpe=Me2PCH2CH2PMe2). Organometallics 28:2385–2390
42.
Zurück zum Zitat Jessop PG (2007) Homogeneous hydrogenation of carbon dioxide. In: Handbook of homogeneous hydrogenation, Chap 17. Wiley-VCH, Weinheim, pp 489–511 Jessop PG (2007) Homogeneous hydrogenation of carbon dioxide. In: Handbook of homogeneous hydrogenation, Chap 17. Wiley-VCH, Weinheim, pp 489–511
43.
Zurück zum Zitat Darensbourg D, Kyran SJ, Yeung AD, Bengali AA (2013) Kinetic and thermodynamic investigation of CO2 insertion into the Ru-Me and Ru-H bonds. An experimental and computational study. Eur J Inorg Chem 4024–4031 Darensbourg D, Kyran SJ, Yeung AD, Bengali AA (2013) Kinetic and thermodynamic investigation of CO2 insertion into the Ru-Me and Ru-H bonds. An experimental and computational study. Eur J Inorg Chem 4024–4031
44.
Zurück zum Zitat Darensbourg DJ, Holtcamp MW (1995) Catalytic activity of zinc(II) phenoxides which possess readily accessible coordination sites. Copolymerization and terpolymerization of epoxides and carbon dioxide. Macromolecules 28:7577–7579 Darensbourg DJ, Holtcamp MW (1995) Catalytic activity of zinc(II) phenoxides which possess readily accessible coordination sites. Copolymerization and terpolymerization of epoxides and carbon dioxide. Macromolecules 28:7577–7579
45.
Zurück zum Zitat Super M, Berluche E, Costello C, Beckman E (1997) Copolymerization of 1,2-epoxycyclohexane and carbon dioxide using carbon dioxide as both reactant and solvent. Macromolecules 30:368–372 Super M, Berluche E, Costello C, Beckman E (1997) Copolymerization of 1,2-epoxycyclohexane and carbon dioxide using carbon dioxide as both reactant and solvent. Macromolecules 30:368–372
46.
Zurück zum Zitat Super M, Beckman E (1998) Copolymerization of CO2 and cyclohexene oxide. J Macromol Symp 127:89–108 Super M, Beckman E (1998) Copolymerization of CO2 and cyclohexene oxide. J Macromol Symp 127:89–108
47.
Zurück zum Zitat Cheng M, Lobkovsky EB, Coates GW (1998) Catalytic reactions involving C1 feedstocks: new high-activity Zn(II)-based catalysts for the alternating copolymerization of carbon dioxide and epoxides. J Am Chem Soc 120:11018–11019 Cheng M, Lobkovsky EB, Coates GW (1998) Catalytic reactions involving C1 feedstocks: new high-activity Zn(II)-based catalysts for the alternating copolymerization of carbon dioxide and epoxides. J Am Chem Soc 120:11018–11019
48.
Zurück zum Zitat Beckman E (1999) Making polymers from carbon dioxide. Science 283:946–947 Beckman E (1999) Making polymers from carbon dioxide. Science 283:946–947
49.
Zurück zum Zitat Darensbourg DJ, Holtcamp MW, Struck GE, Zimmer MS, Niezgoda SA, Rainey P, Robertson JB, Draper JD, Reibenspies JH (1999) Catalytic activity of a series of Zn(II) phenoxides for the copolymerization of epoxides and carbon dioxide. J Am Chem Soc 121:107–116 Darensbourg DJ, Holtcamp MW, Struck GE, Zimmer MS, Niezgoda SA, Rainey P, Robertson JB, Draper JD, Reibenspies JH (1999) Catalytic activity of a series of Zn(II) phenoxides for the copolymerization of epoxides and carbon dioxide. J Am Chem Soc 121:107–116
50.
Zurück zum Zitat Darensbourg DJ, Wildeson JR, Yarbrough JC, Reibenspies JH (2000) Bis 2,6-difluorophenoxide dimeric complexes of zinc and cadmium and their phosphine adducts: lessons learned relative to carbon dioxide/cyclohexene oxide alternating copolymerization processes catalyzed by zinc phenoxides. J Am Chem Soc 122:12487–12496 Darensbourg DJ, Wildeson JR, Yarbrough JC, Reibenspies JH (2000) Bis 2,6-difluorophenoxide dimeric complexes of zinc and cadmium and their phosphine adducts: lessons learned relative to carbon dioxide/cyclohexene oxide alternating copolymerization processes catalyzed by zinc phenoxides. J Am Chem Soc 122:12487–12496
51.
Zurück zum Zitat Cheng M, Moore DR, Reczek JJ, Chamberlain BM, Lobkovsky BE, Coates GW (2001) Single-site β-diiminate zinc catalysts for the alternating copolymerization of CO2 and epoxides: catalyst synthesis and unprecedented polymerization activity. J Am Chem Soc 123:8738–8749 Cheng M, Moore DR, Reczek JJ, Chamberlain BM, Lobkovsky BE, Coates GW (2001) Single-site β-diiminate zinc catalysts for the alternating copolymerization of CO2 and epoxides: catalyst synthesis and unprecedented polymerization activity. J Am Chem Soc 123:8738–8749
52.
Zurück zum Zitat Cheng M, Darling NA, Lobkovsky EB, Coates GW (2000) Enantiomerically-enriched organic reagents via polymer synthesis: enantioselective copolymerization of cycloalkene oxides and CO2 using homogeneous, zinc-based catalysts. Chem Commun 2007–2008 Cheng M, Darling NA, Lobkovsky EB, Coates GW (2000) Enantiomerically-enriched organic reagents via polymer synthesis: enantioselective copolymerization of cycloalkene oxides and CO2 using homogeneous, zinc-based catalysts. Chem Commun 2007–2008
53.
Zurück zum Zitat Eberhardt R, Allmendinger M, Luinstra GA, Rieger B (2000) The ethylsulfinate ligand: a highly efficient initiating group for the zinc β-diiminate catalyzed copolymerization reaction of CO2 and epoxides. Organometallics 22:211–214 Eberhardt R, Allmendinger M, Luinstra GA, Rieger B (2000) The ethylsulfinate ligand: a highly efficient initiating group for the zinc β-diiminate catalyzed copolymerization reaction of CO2 and epoxides. Organometallics 22:211–214
54.
Zurück zum Zitat Inoue S (2000) Immortal polymerization: the outset, development, and application. J Polym Sci A 38:2861–2871 Inoue S (2000) Immortal polymerization: the outset, development, and application. J Polym Sci A 38:2861–2871
55.
Zurück zum Zitat Kruper WJ, Dellar DV (1995) Catalytic formation of cyclic carbonates from epoxides and CO2 with chromium metalloporphyrinates. J Org Chem 60:725–727 Kruper WJ, Dellar DV (1995) Catalytic formation of cyclic carbonates from epoxides and CO2 with chromium metalloporphyrinates. J Org Chem 60:725–727
56.
Zurück zum Zitat Mang S, Cooper AI, Colclough ME, Chauhan N, Holmes A (2000) Copolymerization of CO2 and 1,2-cyclohexene oxide using a CO2-soluble chromium porphyrin catalyst. Macromolecules 33:303–308 Mang S, Cooper AI, Colclough ME, Chauhan N, Holmes A (2000) Copolymerization of CO2 and 1,2-cyclohexene oxide using a CO2-soluble chromium porphyrin catalyst. Macromolecules 33:303–308
57.
Zurück zum Zitat Allen SD, Moore DR, Lobkovsky EB, Coates GW (2002) High-activity, single-site catalysts for the alternating copolymerization of CO2 and propylene oxide. J Am Chem Soc 124:14284–14285 Allen SD, Moore DR, Lobkovsky EB, Coates GW (2002) High-activity, single-site catalysts for the alternating copolymerization of CO2 and propylene oxide. J Am Chem Soc 124:14284–14285
58.
Zurück zum Zitat Darensbourg DJ, Lewis SJ, Rodgers JL, Yarbrough JC (2003) Carbon dioxide/epoxide coupling reactions utilizing Lewis base adducts of zinc halides as catalysts. Cyclic carbonate versus polycarbonate production. Inorg Chem 42:581–589 Darensbourg DJ, Lewis SJ, Rodgers JL, Yarbrough JC (2003) Carbon dioxide/epoxide coupling reactions utilizing Lewis base adducts of zinc halides as catalysts. Cyclic carbonate versus polycarbonate production. Inorg Chem 42:581–589
59.
Zurück zum Zitat Darensbourg DJ, Yarbrough JC (2002) Mechanistic aspects of the copolymerization reaction of carbon dioxide and epoxides, using a chiral salen chromium chloride catalyst. J Am Chem Soc 124:6335–6342 Darensbourg DJ, Yarbrough JC (2002) Mechanistic aspects of the copolymerization reaction of carbon dioxide and epoxides, using a chiral salen chromium chloride catalyst. J Am Chem Soc 124:6335–6342
60.
Zurück zum Zitat Eberhardt R, Allmendinger M, Rieger B (2003) DMAP/Cr(III) catalyst ratio: the decisive factor for poly(propylene carbonate) formation in the coupling of CO2 and propylene oxide. Macromol Rapid Commun 24:194–196 Eberhardt R, Allmendinger M, Rieger B (2003) DMAP/Cr(III) catalyst ratio: the decisive factor for poly(propylene carbonate) formation in the coupling of CO2 and propylene oxide. Macromol Rapid Commun 24:194–196
61.
Zurück zum Zitat Darensbourg DJ, Yarbrough JC, Ortiz C, Fang CC (2003) Comparative kinetic studies of the copolymerization of cyclohexene oxide and propylene oxide with carbon dioxide in the presence of chromium salen derivatives. In situ FTIR measurements of copolymer vs cyclic carbonate production. J Am Chem Soc 125:7586–7591 Darensbourg DJ, Yarbrough JC, Ortiz C, Fang CC (2003) Comparative kinetic studies of the copolymerization of cyclohexene oxide and propylene oxide with carbon dioxide in the presence of chromium salen derivatives. In situ FTIR measurements of copolymer vs cyclic carbonate production. J Am Chem Soc 125:7586–7591
62.
Zurück zum Zitat Darensbourg DJ, Sanchez KM, Reibenspies JH, Rheingold AL (1989) Synthesis, structure, and reactivity of zerovalent group 6 metal pentacarbonyl aryl oxide complexes. Reactions with carbon dioxide. J Am Chem Soc 111:7094–7103 Darensbourg DJ, Sanchez KM, Reibenspies JH, Rheingold AL (1989) Synthesis, structure, and reactivity of zerovalent group 6 metal pentacarbonyl aryl oxide complexes. Reactions with carbon dioxide. J Am Chem Soc 111:7094–7103
63.
Zurück zum Zitat Simpson RD, Bergman RG (1992) A dramatic difference in the reactivities of alkoxido- and aryloxidorhenium complexes in insertion reactions. Angew Chem Int Ed Engl 31:220–223 Simpson RD, Bergman RG (1992) A dramatic difference in the reactivities of alkoxido- and aryloxidorhenium complexes in insertion reactions. Angew Chem Int Ed Engl 31:220–223
64.
Zurück zum Zitat Darensbourg DJ, Lee WZ, Phelps AL, Guidry E (2003) Kinetic study of the insertion and deinsertion of carbon dioxide into fac-(CO)3(dppe)MnOR derivatives. Organometallics 22:5585–5588 Darensbourg DJ, Lee WZ, Phelps AL, Guidry E (2003) Kinetic study of the insertion and deinsertion of carbon dioxide into fac-(CO)3(dppe)MnOR derivatives. Organometallics 22:5585–5588
65.
Zurück zum Zitat Mandal SK, Ho DM, Orchin M (1991) A convenient synthesis of the manganese and rhenium alkoxides and phenoxides fac-(CO)3(dppe)MOR (R = CH3, C2H5, C6H5; dppe=1,2-bis(diphenylphosphino)ethane). X-Ray structure of fac-(CO)3(dppe)ReOC6H5. Inorg Chem 30:2244–2248 Mandal SK, Ho DM, Orchin M (1991) A convenient synthesis of the manganese and rhenium alkoxides and phenoxides fac-(CO)3(dppe)MOR (R = CH3, C2H5, C6H5; dppe=1,2-bis(diphenylphosphino)ethane). X-Ray structure of fac-(CO)3(dppe)ReOC6H5. Inorg Chem 30:2244–2248
66.
Zurück zum Zitat Mandal SK, Ho DM, Orchin M (1993) Reaction of electrophiles with manganese(I) and rhenium(I) alkoxide complexes: reversible absorption of atmospheric carbon dioxide. Organometallics 12:1714–1719 Mandal SK, Ho DM, Orchin M (1993) Reaction of electrophiles with manganese(I) and rhenium(I) alkoxide complexes: reversible absorption of atmospheric carbon dioxide. Organometallics 12:1714–1719
67.
Zurück zum Zitat Aresta M, Dibenedetto A, Pastore C (2003) Synthesis and characterization of Nb(OR)4[OC(O)OR] (R = Me, Et, Allyl) and their reaction with the parent alcohol to afford organic carbonates. Inorg Chem 42:3256–3261 Aresta M, Dibenedetto A, Pastore C (2003) Synthesis and characterization of Nb(OR)4[OC(O)OR] (R = Me, Et, Allyl) and their reaction with the parent alcohol to afford organic carbonates. Inorg Chem 42:3256–3261
68.
Zurück zum Zitat Elmas S, Subhani MA, Vogt H, Leitner W, Muller T (2013) Facile insertion of CO2 into metal-phenoxide bond. Green Chem 15:1356–1360 Elmas S, Subhani MA, Vogt H, Leitner W, Muller T (2013) Facile insertion of CO2 into metal-phenoxide bond. Green Chem 15:1356–1360
69.
Zurück zum Zitat Hayward PJ, Blake DM, Nyman CJ, Wilkinson G (1969) Some novel peroxocarbonate complexes of platinum (II). J Chem Soc D Chem Commun 17:987–988 Hayward PJ, Blake DM, Nyman CJ, Wilkinson G (1969) Some novel peroxocarbonate complexes of platinum (II). J Chem Soc D Chem Commun 17:987–988
70.
Zurück zum Zitat Hayward PJ, Blake DM, Wilkinson G, Nyman CJ (1970) Reactions of peroxobis(triphenylphosphine) platinum (II) and analogs with carbon dioxide, carbon disulfide, and other unsaturated molecules. J Am Chem Soc 92:5873–5878 Hayward PJ, Blake DM, Wilkinson G, Nyman CJ (1970) Reactions of peroxobis(triphenylphosphine) platinum (II) and analogs with carbon dioxide, carbon disulfide, and other unsaturated molecules. J Am Chem Soc 92:5873–5878
71.
Zurück zum Zitat Dahlenburg L, Prengel C (1984) Alkyl and aryl compounds of iridium and rhodium. 18. Oligophosphine ligands. 6. Reactivity of some alkyls and aryls of rhodium and iridium toward carbon dioxide. Facile formation and X-ray structural characterization of the peroxocarbonato complex [cyclic]-mer- [PhP(CH2CH2CH2PPh2)2]. Organometallics 3:934–936 Dahlenburg L, Prengel C (1984) Alkyl and aryl compounds of iridium and rhodium. 18. Oligophosphine ligands. 6. Reactivity of some alkyls and aryls of rhodium and iridium toward carbon dioxide. Facile formation and X-ray structural characterization of the peroxocarbonato complex [cyclic]-mer- https://static-content.springer.com/image/chp%3A10.1007%2F978-3-662-46831-9_4/MediaObjects/218178_1_En_4_Figa_HTML.gif [PhP(CH2CH2CH2PPh2)2]. Organometallics 3:934–936
72.
Zurück zum Zitat Aresta M, Quaranta E, Ciccarese A (1985) Rhodium (I) promoted activation of carbon dioxide. C1 Mol Chem 1:267–281 Aresta M, Quaranta E, Ciccarese A (1985) Rhodium (I) promoted activation of carbon dioxide. C1 Mol Chem 1:267–281
73.
Zurück zum Zitat Aresta M, Tommasi I, Quaranta E, Fragale C, Mascetti J, Tranquille M, Galan F, Fouassier M (1996) Mechanism of formation of peroxocarbonates and their reactivity as oxygen transfer agents mimicking monooxygenases. The first evidence of CO2 insertion into the O-O bond of Rh(η2-O2) complexes. Inorg Chem 35:4254–4260 Aresta M, Tommasi I, Quaranta E, Fragale C, Mascetti J, Tranquille M, Galan F, Fouassier M (1996) Mechanism of formation of peroxocarbonates https://static-content.springer.com/image/chp%3A10.1007%2F978-3-662-46831-9_4/MediaObjects/218178_1_En_4_Figb_HTML.gif and their reactivity as oxygen transfer agents mimicking monooxygenases. The first evidence of CO2 insertion into the O-O bond of Rh(η2-O2) complexes. Inorg Chem 35:4254–4260
74.
Zurück zum Zitat Aresta M, Quaranta E, Tommasi I, Mascetti J, Tranquille M, Borowiak M (1998) Formation of peroxocarbonates from L3Rh(O2)Cl and L2Ni(CO2): a unique reaction mechanism with carbon dioxide insertion into the O-O bond. Stud Surf Sci Catal 114:677–680 Aresta M, Quaranta E, Tommasi I, Mascetti J, Tranquille M, Borowiak M (1998) Formation of peroxocarbonates from L3Rh(O2)Cl and L2Ni(CO2): a unique reaction mechanism with carbon dioxide insertion into the O-O bond. Stud Surf Sci Catal 114:677–680
75.
Zurück zum Zitat Borowiak MA, Jamroz MH, Dobrowolski JC, Bajdor K, Kazimirski JK, Mascetti J, Quaranta E, Tommasi I, Aresta M (2001) Application of the impulse oscillation model for modeling the formation of peroxocarbonates via carbon dioxide reaction with dioxygen transition metal complexes. A comparison with the experimental results obtained for Rh(η2-O2)ClP3 [P = phosphane ligand]. J Mol Catal A 165:45–54 Borowiak MA, Jamroz MH, Dobrowolski JC, Bajdor K, Kazimirski JK, Mascetti J, Quaranta E, Tommasi I, Aresta M (2001) Application of the impulse oscillation model for modeling the formation of peroxocarbonates via carbon dioxide reaction with dioxygen transition metal complexes. A comparison with the experimental results obtained for Rh(η2-O2)ClP3 [P = phosphane ligand]. J Mol Catal A 165:45–54
77.
Zurück zum Zitat Aresta M, Tommasi I, Dibenedetto A, Fouassier M, Mascetti J (2002) Mechanism of formation of the peroxocarbonate complex (PCy3)2Ni(CO4) from solid (PCy3)2Ni(CO2) and dioxygen: an example of solid-state metallorganic reaction involving CO2 deco-ordination and reinsertion into the O-O bond of (PCy3)2Ni(O2). Reactivity of the peroxocarbonate complex towards olefins in the solid state and in solution. Inorg Chim Acta 330:63–71 Aresta M, Tommasi I, Dibenedetto A, Fouassier M, Mascetti J (2002) Mechanism of formation of the peroxocarbonate complex (PCy3)2Ni(CO4) from solid (PCy3)2Ni(CO2) and dioxygen: an example of solid-state metallorganic reaction involving CO2 deco-ordination and reinsertion into the O-O bond of (PCy3)2Ni(O2). Reactivity of the peroxocarbonate complex towards olefins in the solid state and in solution. Inorg Chim Acta 330:63–71
78.
Zurück zum Zitat Yin X, Moss JR (1999) Recent developments in the activation of carbon dioxide by metal complexes. Coord Chem Rev 181:27–59 Yin X, Moss JR (1999) Recent developments in the activation of carbon dioxide by metal complexes. Coord Chem Rev 181:27–59
79.
Zurück zum Zitat Behr A (1988) Carbon dioxide as an alternative C1 synthetic unit: activation by transition metal complexes. Angew Chem Int Ed Engl 27:661–678 Behr A (1988) Carbon dioxide as an alternative C1 synthetic unit: activation by transition metal complexes. Angew Chem Int Ed Engl 27:661–678
80.
Zurück zum Zitat Walther D, Ruben M, Rau S (1999) Carbon dioxide and metal centres: from reactions inspired by nature to reactions in compressed carbon dioxide as solvent. Coord Chem Rev 182:67–100 Walther D, Ruben M, Rau S (1999) Carbon dioxide and metal centres: from reactions inspired by nature to reactions in compressed carbon dioxide as solvent. Coord Chem Rev 182:67–100
81.
Zurück zum Zitat Schenk S, Notni J, Kohn U, Wermann K, Anders E (2006) Carbon dioxide and related heterocumulenes at zinc and lithium cations: bioinspired reactions and principles. Dalton Trans 4191–4206 Schenk S, Notni J, Kohn U, Wermann K, Anders E (2006) Carbon dioxide and related heterocumulenes at zinc and lithium cations: bioinspired reactions and principles. Dalton Trans 4191–4206
82.
Zurück zum Zitat Belli Dell’Amico D, Calderazzo F, Labella L, Marchetti F, Pampaloni G (2003) Converting carbon dioxide into carbamato derivatives. Chem Rev 103:3857–3897 Belli Dell’Amico D, Calderazzo F, Labella L, Marchetti F, Pampaloni G (2003) Converting carbon dioxide into carbamato derivatives. Chem Rev 103:3857–3897
83.
Zurück zum Zitat Quaranta E, Aresta M (2010) The chemistry of N-CO2 bonds: synthesis of carbamic acids and their derivatives, isocyanates, and ureas. In: Aresta M (ed) Carbon dioxide as chemical feedstock. Wiley-VCH, Weinheim, pp 121–167 Quaranta E, Aresta M (2010) The chemistry of N-CO2 bonds: synthesis of carbamic acids and their derivatives, isocyanates, and ureas. In: Aresta M (ed) Carbon dioxide as chemical feedstock. Wiley-VCH, Weinheim, pp 121–167
84.
Zurück zum Zitat Matson EM, Fanwick PE, Bart SC (2011) Formation of trivalent U-C, U-N, and U-S bonds and their reactivity towards carbon dioxide and acetone. Organometallics 30:5753–5762 Matson EM, Fanwick PE, Bart SC (2011) Formation of trivalent U-C, U-N, and U-S bonds and their reactivity towards carbon dioxide and acetone. Organometallics 30:5753–5762
85.
Zurück zum Zitat Chisolm MH, Extine M (1975) Carbon dioxide exchange reactions involving transition-metal N,N-dimethylcarbamato compounds: reversible insertion of carbon dioxide into transition-metal-nitrogen σ bonds. J Chem Soc Chem Commun 438–439 Chisolm MH, Extine M (1975) Carbon dioxide exchange reactions involving transition-metal N,N-dimethylcarbamato compounds: reversible insertion of carbon dioxide into transition-metal-nitrogen σ bonds. J Chem Soc Chem Commun 438–439
86.
Zurück zum Zitat Chisolm MH, Extine M (1977) Reactions of transition metal-nitrogen σ bonds. 4. Mechanistic studies of carbon dioxide insertion and carbon dioxide exchange reactions involving early transition-metal dimethylamido and N, N-dimethylcarbamato compounds. J Am Chem Soc 99:792–802 Chisolm MH, Extine M (1977) Reactions of transition metal-nitrogen σ bonds. 4. Mechanistic studies of carbon dioxide insertion and carbon dioxide exchange reactions involving early transition-metal dimethylamido and N, N-dimethylcarbamato compounds. J Am Chem Soc 99:792–802
87.
Zurück zum Zitat Chisolm MH, Extine M (1977) Reactions of transition metal-nitrogen σ bonds. 3. Transition metal N, N-dimethylcarbamates. Preparation, properties, and carbon dioxide exchange reactions. J Am Chem Soc 99:782–792 Chisolm MH, Extine M (1977) Reactions of transition metal-nitrogen σ bonds. 3. Transition metal N, N-dimethylcarbamates. Preparation, properties, and carbon dioxide exchange reactions. J Am Chem Soc 99:782–792
88.
Zurück zum Zitat Remko M, Rode BM (1995) Ab initio study of decomposition of carbamic acid and its thio and sila derivatives. J Mol Struct (Theochem) 339:125–131 Remko M, Rode BM (1995) Ab initio study of decomposition of carbamic acid and its thio and sila derivatives. J Mol Struct (Theochem) 339:125–131
89.
Zurück zum Zitat Andrés J, Moliner V, Krecbl J, Silla E (1994) Comparison of several semiempirical and ab initio methods for transition state structure characterization. Addition of CO2 to CH3NHCONH2. J Phys Chem 98:3664–3668 Andrés J, Moliner V, Krecbl J, Silla E (1994) Comparison of several semiempirical and ab initio methods for transition state structure characterization. Addition of CO2 to CH3NHCONH2. J Phys Chem 98:3664–3668
90.
Zurück zum Zitat Andrés J, Moliner V, Krecbl J, Silla E (1993) A theoretical study of the addition mechanism of carbon dioxide to methylamine. Modelling CO2–biotin fixation. J Chem Soc Perkin Trans 2:521–523 Andrés J, Moliner V, Krecbl J, Silla E (1993) A theoretical study of the addition mechanism of carbon dioxide to methylamine. Modelling CO2–biotin fixation. J Chem Soc Perkin Trans 2:521–523
91.
Zurück zum Zitat Andrés J, Moliner V, Krecbl J, Silla E (1993) A theoretical study of the effect of basis sets on stationary structures for the addition of carbon dioxide to methylamine: a relation among geometries, energy status, and electronic structures. Int J Quantum Chem 45:433–444 Andrés J, Moliner V, Krecbl J, Silla E (1993) A theoretical study of the effect of basis sets on stationary structures for the addition of carbon dioxide to methylamine: a relation among geometries, energy status, and electronic structures. Int J Quantum Chem 45:433–444
92.
Zurück zum Zitat Chakraborty AK, Bischoff KB, Astarita G, Damewood JR (1988) Molecular orbital approach to substituent effects in amine-CO2 interactions. J Am Chem Soc 110:6947–6954 Chakraborty AK, Bischoff KB, Astarita G, Damewood JR (1988) Molecular orbital approach to substituent effects in amine-CO2 interactions. J Am Chem Soc 110:6947–6954
93.
Zurück zum Zitat Jamróz MH, Dobrowolski JC, Borowiak MA (1997) Ab initio study on the 1:2 reaction of CO2 with dimethylamine. J Mol Struct 404:105–111 Jamróz MH, Dobrowolski JC, Borowiak MA (1997) Ab initio study on the 1:2 reaction of CO2 with dimethylamine. J Mol Struct 404:105–111
94.
Zurück zum Zitat Jamróz MH, Dobrowolski JC, Borowiak MA (1999) The CO2 with dimethylamine reaction: ab initio predicted vibrational spectra. J Mol Struct 482–483:633–637 Jamróz MH, Dobrowolski JC, Borowiak MA (1999) The CO2 with dimethylamine reaction: ab initio predicted vibrational spectra. J Mol Struct 482–483:633–637
95.
Zurück zum Zitat Jamróz MH, Dobrowolski JC, Borowiak MA (2000) Theoretical IR spectra of the (2:1) ammonia–carbon dioxide system. Vib Spectrosc 22:157–161 Jamróz MH, Dobrowolski JC, Borowiak MA (2000) Theoretical IR spectra of the (2:1) ammonia–carbon dioxide system. Vib Spectrosc 22:157–161
96.
Zurück zum Zitat Masuda K, Ito Y, Horiguchi M, Fujita H (2005) Studies on the solvent dependence of the carbamic acid formation from ω-(1-naphthyl)alkylamines and carbon dioxide. Tetrahedron 61:213–229 Masuda K, Ito Y, Horiguchi M, Fujita H (2005) Studies on the solvent dependence of the carbamic acid formation from ω-(1-naphthyl)alkylamines and carbon dioxide. Tetrahedron 61:213–229
97.
Zurück zum Zitat Hampe EM, Rudkevich DM (2003) Exploring reversible reactions between CO2 and amines. Tetrahedron 59:9619–9625 Hampe EM, Rudkevich DM (2003) Exploring reversible reactions between CO2 and amines. Tetrahedron 59:9619–9625
98.
Zurück zum Zitat Wittmann K, Wisniewski W, Mynott R, Leitner W, Kranermann CL, Rische T, Eilbracht P, Kluwer S, Ernsting JM, Elsevier CJ (2001) Supercritical carbon dioxide as solvent and temporary protecting group for Rhodium-catalyzed hydroaminomethylation. Chem Eur J 7:4584–4589 Wittmann K, Wisniewski W, Mynott R, Leitner W, Kranermann CL, Rische T, Eilbracht P, Kluwer S, Ernsting JM, Elsevier CJ (2001) Supercritical carbon dioxide as solvent and temporary protecting group for Rhodium-catalyzed hydroaminomethylation. Chem Eur J 7:4584–4589
99.
Zurück zum Zitat Furstner A, Ackermann L, Beck K, Hori H, Koch D, Langemann K, Liebl M, Six C, Leitner W (2001) Olefin metathesis in supercritical carbon dioxide. J Am Chem Soc 123:9000–9006 Furstner A, Ackermann L, Beck K, Hori H, Koch D, Langemann K, Liebl M, Six C, Leitner W (2001) Olefin metathesis in supercritical carbon dioxide. J Am Chem Soc 123:9000–9006
100.
Zurück zum Zitat Xie X, Liotta CL, Eckert CA (2004) CO2-protected amine formation from nitrile and imine hydrogenation in gas-expanded liquids. Ind Eng Chem Res 43:7907–7911 Xie X, Liotta CL, Eckert CA (2004) CO2-protected amine formation from nitrile and imine hydrogenation in gas-expanded liquids. Ind Eng Chem Res 43:7907–7911
101.
Zurück zum Zitat Fischer H, Gyllenhaal O, Vessmann J, Albert K (2003) Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography. Anal Chem 75:622–626 Fischer H, Gyllenhaal O, Vessmann J, Albert K (2003) Reaction monitoring of aliphatic amines in supercritical carbon dioxide by proton nuclear magnetic resonance spectroscopy and implications for supercritical fluid chromatography. Anal Chem 75:622–626
102.
Zurück zum Zitat Dijkstra ZJ, Doornbos AR, Weyten H, Ernsting JM, Elsevier CJ, Keurentjes JTF (2007) Formation of carbamic acid in organic solvents and in supercritical carbon dioxide. J Supercrit Fluids 41:109–114 Dijkstra ZJ, Doornbos AR, Weyten H, Ernsting JM, Elsevier CJ, Keurentjes JTF (2007) Formation of carbamic acid in organic solvents and in supercritical carbon dioxide. J Supercrit Fluids 41:109–114
103.
Zurück zum Zitat Kayaki Y, Suzuki T, Ikariya T (2008) Utilization of N, N-dialkylcarbamic acid derived from secondary amines and supercritical carbon dioxide: stereoselective synthesis of Z alkenyl carbamates with a CO2-soluble ruthenium–P(OC2H5)3 catalyst. Chem Asian J 3:1865–1870 Kayaki Y, Suzuki T, Ikariya T (2008) Utilization of N, N-dialkylcarbamic acid derived from secondary amines and supercritical carbon dioxide: stereoselective synthesis of Z alkenyl carbamates with a CO2-soluble ruthenium–P(OC2H5)3 catalyst. Chem Asian J 3:1865–1870
104.
Zurück zum Zitat Aresta M, Ballivet-Tkatchenko D, Bonnet MC, Faure R, Loiseleur H (1985) Synthesis and structural characterization of Co(NO)2[PhP(OCH2CH2)2NH]Cl: a novel carbon dixide carrier. J Am Chem Soc 107:2994–2995 Aresta M, Ballivet-Tkatchenko D, Bonnet MC, Faure R, Loiseleur H (1985) Synthesis and structural characterization of Co(NO)2[PhP(OCH2CH2)2NH]Cl: a novel carbon dixide carrier. J Am Chem Soc 107:2994–2995
105.
Zurück zum Zitat Aresta M, Ballivet-Tkatchenko D, Belli Dell’Amico D, Bonnet MC, Boschi D, Calderazzo F, Faure R, Labella L, Marchetti F (1985) Isolation and structural determination of two derivatives of the elusive carbamic acid. Chem Commun 1099–1100 Aresta M, Ballivet-Tkatchenko D, Belli Dell’Amico D, Bonnet MC, Boschi D, Calderazzo F, Faure R, Labella L, Marchetti F (1985) Isolation and structural determination of two derivatives of the elusive carbamic acid. Chem Commun 1099–1100
106.
Zurück zum Zitat Jamróz MH, Dobrowolski JC (2002) Theoretical IR spectra and stability of carbamic acid complexes. Vib Spectrosc 29:217–221 Jamróz MH, Dobrowolski JC (2002) Theoretical IR spectra and stability of carbamic acid complexes. Vib Spectrosc 29:217–221
107.
Zurück zum Zitat Jamróz MH, Dobrowolski JC, Rode JE, Borowiak MA (2002) Comparison of calculated structural parameters and infrared spectra with experimental data for dimeric dibenzyl carbamic acid. J Mol Struct (Theochem) 618:101–108 Jamróz MH, Dobrowolski JC, Rode JE, Borowiak MA (2002) Comparison of calculated structural parameters and infrared spectra with experimental data for dimeric dibenzyl carbamic acid. J Mol Struct (Theochem) 618:101–108
108.
Zurück zum Zitat Aresta M, Quaranta E (1992) Role of the macrocyclic polyether in the synthesis of N-alkylcarbamate esters from primary amines, CO2 and alkyl halides in the presence of crown-ethers. Tetrahedron 48:1515–1530 Aresta M, Quaranta E (1992) Role of the macrocyclic polyether in the synthesis of N-alkylcarbamate esters from primary amines, CO2 and alkyl halides in the presence of crown-ethers. Tetrahedron 48:1515–1530
109.
Zurück zum Zitat Darensbourg DJ, Frost BJ, Larkins DL (2001) An experimental and theoretical investigation of the carbon dioxide insertion process into the tungsten-nitrogen bond of an anionic W(0) complex. Inorg Chem 40:1993–1999 Darensbourg DJ, Frost BJ, Larkins DL (2001) An experimental and theoretical investigation of the carbon dioxide insertion process into the tungsten-nitrogen bond of an anionic W(0) complex. Inorg Chem 40:1993–1999
110.
Zurück zum Zitat Park S, Rheingold AL, Roundhill DM (1991) Synthesis and reaction chemistry of monomeric and dimeric amide complexes of platinum(II). Organometallics 10:615–623 Park S, Rheingold AL, Roundhill DM (1991) Synthesis and reaction chemistry of monomeric and dimeric amide complexes of platinum(II). Organometallics 10:615–623
111.
Zurück zum Zitat Hartwig JF, Bergman RG, Andersen RA (1991) Insertion reactions of CO and CO2 with ruthenium benzyl, arylamido, and aryloxide complexes: a comparison of the reactivity of ruthenium-carbon, ruthenium-nitrogen, and ruthenium-oxygen bonds. J Am Chem Soc 113:6499–6508 Hartwig JF, Bergman RG, Andersen RA (1991) Insertion reactions of CO and CO2 with ruthenium benzyl, arylamido, and aryloxide complexes: a comparison of the reactivity of ruthenium-carbon, ruthenium-nitrogen, and ruthenium-oxygen bonds. J Am Chem Soc 113:6499–6508
112.
Zurück zum Zitat Cowan RL, Trogler WC (1989) Syntheses, reactions and molecular structures of trans-hydrido(phenylamido)bis(triethylphosphine)platinum(II) and trans-hydridophenoxobis(triethylphosphine)platinum(II). J Am Chem Soc 111:4750–4761 Cowan RL, Trogler WC (1989) Syntheses, reactions and molecular structures of trans-hydrido(phenylamido)bis(triethylphosphine)platinum(II) and trans-hydridophenoxobis(triethylphosphine)platinum(II). J Am Chem Soc 111:4750–4761
113.
Zurück zum Zitat Legzdins P, Rettig SJ, Ross KJ (1994) Competitive reactivity of W-C, W-N, and W-O bonds at the Cp*W(NO) fragment: insertion reactions of tert-butyl isocyanide, p-tolyl isocyanate, and carbon disulfide. Organometallics 13:569–577 Legzdins P, Rettig SJ, Ross KJ (1994) Competitive reactivity of W-C, W-N, and W-O bonds at the Cp*W(NO) fragment: insertion reactions of tert-butyl isocyanide, p-tolyl isocyanate, and carbon disulfide. Organometallics 13:569–577
114.
Zurück zum Zitat Andersen RA (1979) Dialkylbis[bis(trimethylsilyl)amido]zirconium(IV) and -hafnium(IV). Preparation and reaction with carbon dioxide and tert-butylisocyanide. Inorg Chem 18:2928–2932 Andersen RA (1979) Dialkylbis[bis(trimethylsilyl)amido]zirconium(IV) and -hafnium(IV). Preparation and reaction with carbon dioxide and tert-butylisocyanide. Inorg Chem 18:2928–2932
115.
Zurück zum Zitat Kloppenburg L, Petersen JL (1996) Facile conversion of an appended silylamido to a silyloxy ligand via isocyanate elimination. Synthesis of {[(C5Me4)SiMe2O]Zr(η2-O2CMe)(μ-O2CMe)}2 via the carboxylation of [(C5Me4)SiMe2(N-t-Bu)]ZrMe2. Organometallics 15:7–9 Kloppenburg L, Petersen JL (1996) Facile conversion of an appended silylamido to a silyloxy ligand via isocyanate elimination. Synthesis of {[(C5Me4)SiMe2O]Zr(η2-O2CMe)(μ-O2CMe)}2 via the carboxylation of [(C5Me4)SiMe2(N-t-Bu)]ZrMe2. Organometallics 15:7–9
116.
Zurück zum Zitat Nieves JS, Royo P (2001) Insertion of carbon dioxide and isocyanide into tantalum-amide and tantalum-methyl bonds. J Organomet Chem 621:299–303 Nieves JS, Royo P (2001) Insertion of carbon dioxide and isocyanide into tantalum-amide and tantalum-methyl bonds. J Organomet Chem 621:299–303
117.
Zurück zum Zitat Ward BD, Orde G, Clot E, Cowley AR, Gade LH, Mountford P (2005) Reactions of neutral and cationic diamide-supported imido complexes with CO2 and other heterocumulenes: issues of site selectivity. Organometallics 24:2368–2385 Ward BD, Orde G, Clot E, Cowley AR, Gade LH, Mountford P (2005) Reactions of neutral and cationic diamide-supported imido complexes with CO2 and other heterocumulenes: issues of site selectivity. Organometallics 24:2368–2385
118.
Zurück zum Zitat Dubberley SR, Friedrich A, Willman DA, Mountford P, Radius U (2003) Synthesis and reactivity of calix[4]arene-supported group 4 imido complexes. Chem Eur J 9:3634–3654 Dubberley SR, Friedrich A, Willman DA, Mountford P, Radius U (2003) Synthesis and reactivity of calix[4]arene-supported group 4 imido complexes. Chem Eur J 9:3634–3654
119.
Zurück zum Zitat Guiducci AE, Boyd CL, Clot E, Mountford P (2009) Reactions of cyclopentadienyl-amidinate titanium imido compounds with CO2: cycloaddition-extrusion vs. cycloaddition-insertion. Dalton Trans 5960–5979 Guiducci AE, Boyd CL, Clot E, Mountford P (2009) Reactions of cyclopentadienyl-amidinate titanium imido compounds with CO2: cycloaddition-extrusion vs. cycloaddition-insertion. Dalton Trans 5960–5979
120.
Zurück zum Zitat Stewart CA, Dickie DA, Tang Y, Kemp RA (2011) Insertion reactions of CO2, OCS and CS2 into the Sn-N bond of (Me2N)2Sn: NMR and X-ray structural characterization of the products. Inorg Chim Acta 376:73–79 Stewart CA, Dickie DA, Tang Y, Kemp RA (2011) Insertion reactions of CO2, OCS and CS2 into the Sn-N bond of (Me2N)2Sn: NMR and X-ray structural characterization of the products. Inorg Chim Acta 376:73–79
121.
Zurück zum Zitat Inoue S, Yokoo Y (1972) Reaction of organoaluminum coordination compounds with carbon dioxide. Bull Chem Soc Jpn 45:3651–3653 Inoue S, Yokoo Y (1972) Reaction of organoaluminum coordination compounds with carbon dioxide. Bull Chem Soc Jpn 45:3651–3653
122.
Zurück zum Zitat Chang C-C, Srinivas B, Mung-Liang W, Wen-Ho C, Chiang MY, Chung-Sheng H (1995) Fixation of CO2 by a series of ethynyl-bridged polynuclear aluminum-magnesium complexes. Synthesis, characterization, and crystal structures of [Me2Al(μ-i-Pr2N)2 Mg(μ-C≡CR)]2 (R = C6H5, C6H4-p-CH3, t-Bu, SiMe3), [Me2Al(μ-Et2N)2 Mg(μ-C≡CC6H5)]2, {(Me2Al)2[μ-OOC(i-Pr2N)]2}, and {(Me2Al)2[(μ-OOC(i-Pr2N))2]2 Mg}. Organometallics 14:5150–5159 Chang C-C, Srinivas B, Mung-Liang W, Wen-Ho C, Chiang MY, Chung-Sheng H (1995) Fixation of CO2 by a series of ethynyl-bridged polynuclear aluminum-magnesium complexes. Synthesis, characterization, and crystal structures of [Me2Al(μ-i-Pr2N)2 Mg(μ-C≡CR)]2 (R = C6H5, C6H4-p-CH3, t-Bu, SiMe3), [Me2Al(μ-Et2N)2 Mg(μ-C≡CC6H5)]2, {(Me2Al)2[μ-OOC(i-Pr2N)]2}, and {(Me2Al)2[(μ-OOC(i-Pr2N))2]2 Mg}. Organometallics 14:5150–5159
123.
Zurück zum Zitat Chang CC, Ameerunisha MS (1999) Chemistry of the organodiamides of magnesium, aluminum and mixed Mg-Al systems. A review of the heterocumulene reactivity on the Mg-Al centers. Coord Chem Rev 189:199–278 Chang CC, Ameerunisha MS (1999) Chemistry of the organodiamides of magnesium, aluminum and mixed Mg-Al systems. A review of the heterocumulene reactivity on the Mg-Al centers. Coord Chem Rev 189:199–278
124.
Zurück zum Zitat Ruben M, Walther D, Knake R, Gorls H, Beckert R (2000) Fixation of carbon dioxide by oxalic amidinato magnesium complexes: structures and reactions of trimetallic magnesium carbamato and related complexes. Eur J Inorg Chem 1055–1064 Ruben M, Walther D, Knake R, Gorls H, Beckert R (2000) Fixation of carbon dioxide by oxalic amidinato magnesium complexes: structures and reactions of trimetallic magnesium carbamato and related complexes. Eur J Inorg Chem 1055–1064
125.
Zurück zum Zitat Tang Y, Zakharov LN, Rheingold AL, Kemp RA (2004) Insertion of carbon dioxide into Mg-N bonds. Structural characterization of a previously unknown η2 chelation mode to magnesium in magnesium carbamates. Organometallics 23:4788–479 Tang Y, Zakharov LN, Rheingold AL, Kemp RA (2004) Insertion of carbon dioxide into Mg-N bonds. Structural characterization of a previously unknown η2 chelation mode to magnesium in magnesium carbamates. Organometallics 23:4788–479
126.
Zurück zum Zitat Davies RP, Raithby PR, Snaith R (1996) A likely intermediate during the CO2-induced activation of 2-alkylindoles toward electrophilic substitution: structure of a unique tetramer formed by joining two boat-shaped (LiOCO)2 rings. Organometallics 15:4355–4356 Davies RP, Raithby PR, Snaith R (1996) A likely intermediate during the CO2-induced activation of 2-alkylindoles toward electrophilic substitution: structure of a unique tetramer formed by joining two boat-shaped (LiOCO)2 rings. Organometallics 15:4355–4356
127.
Zurück zum Zitat Kennedy AR, Mulvey RF, Oliver DF, Robertson SD (2010) Lithium and aluminum carbamato derivatives of the utility amide 2,2,6,6,-tetramethylpiperidide. Dalton Trans 39:6190–6197 Kennedy AR, Mulvey RF, Oliver DF, Robertson SD (2010) Lithium and aluminum carbamato derivatives of the utility amide 2,2,6,6,-tetramethylpiperidide. Dalton Trans 39:6190–6197
128.
Zurück zum Zitat McCowan CS, Groy TL, Caudle MT (2002) Synthesis, structure, and preparative transamination of tetrazinc carbamato complexes having the basic zinc carboxylate structure. Inorg Chem 41:1120–1127 McCowan CS, Groy TL, Caudle MT (2002) Synthesis, structure, and preparative transamination of tetrazinc carbamato complexes having the basic zinc carboxylate structure. Inorg Chem 41:1120–1127
129.
Zurück zum Zitat Tang Y, Kassel WS, Zakharov LN, Rheingold AL, Kemp RA (2005) Insertion of carbon dioxide into Zn-N bonds. Syntheses and structure of tetrameric and dimeric alkylzinc carbamato complexes. Inorg Chem 44:359–364 Tang Y, Kassel WS, Zakharov LN, Rheingold AL, Kemp RA (2005) Insertion of carbon dioxide into Zn-N bonds. Syntheses and structure of tetrameric and dimeric alkylzinc carbamato complexes. Inorg Chem 44:359–364
130.
Zurück zum Zitat Domide D, Kaifer E, Mautz J, Walter O, Behrens S, Himmel H-J (2008) Synthesis and characterisation of some new zinc carbamate complexes formed by CO2 fixation and their use as precursors for ZnO particles under mild conditions. Eur J Inorg Chem 3177–3185 Domide D, Kaifer E, Mautz J, Walter O, Behrens S, Himmel H-J (2008) Synthesis and characterisation of some new zinc carbamate complexes formed by CO2 fixation and their use as precursors for ZnO particles under mild conditions. Eur J Inorg Chem 3177–3185
131.
Zurück zum Zitat Nilsson Lill SO, Kohn U, Anders E (2004) Carbon dioxide fixation by lithium amides: DFT studies on the reaction mechanism of the formation of lithium carbamates. Eur J Org Chem 2868–2880 Nilsson Lill SO, Kohn U, Anders E (2004) Carbon dioxide fixation by lithium amides: DFT studies on the reaction mechanism of the formation of lithium carbamates. Eur J Org Chem 2868–2880
132.
Zurück zum Zitat Himmel H-J (2007) On the mechanism of CO2 insertion into the Mg-N bond of mono- and dinuclears magnesium compound: a quantum chemical study. Z Anorg Allg Chem 633:2191–2198 Himmel H-J (2007) On the mechanism of CO2 insertion into the Mg-N bond of mono- and dinuclears magnesium compound: a quantum chemical study. Z Anorg Allg Chem 633:2191–2198
133.
Zurück zum Zitat Himmel H-J (2007) CO2 fixation by alkyl zinc amides: a quantum chemical study motivated by recent experimental results. Eur J Inorg Chem 675–683 Himmel H-J (2007) CO2 fixation by alkyl zinc amides: a quantum chemical study motivated by recent experimental results. Eur J Inorg Chem 675–683
134.
Zurück zum Zitat Lihs FJ, Caudle MT (2002) Kinetics and mechanism for CO2 scrambling in a N-carboxyimidazolidone analogue for N1-carboxybiotin. J Am Chem Soc 124:11334–11341 Lihs FJ, Caudle MT (2002) Kinetics and mechanism for CO2 scrambling in a N-carboxyimidazolidone analogue for N1-carboxybiotin. J Am Chem Soc 124:11334–11341
135.
Zurück zum Zitat McCowan CS, Caudle MT (2005) Evidence for unimolecular CO2 elimination in C-N metathesis reactions of carbamatozinc complexes Zn4O(O2Cam)6 (Am = N-diethylamino, N-piperidyl, N-pyrrolidyl). Dalton Trans 238–246 McCowan CS, Caudle MT (2005) Evidence for unimolecular CO2 elimination in C-N metathesis reactions of carbamatozinc complexes Zn4O(O2Cam)6 (Am = N-diethylamino, N-piperidyl, N-pyrrolidyl). Dalton Trans 238–246
136.
Zurück zum Zitat Dureen MA, Stephan DW (2010) Reactions of boron amidinates with CO2 and CO and other small molecules. J Am Chem Soc 132:13559–13569 Dureen MA, Stephan DW (2010) Reactions of boron amidinates with CO2 and CO and other small molecules. J Am Chem Soc 132:13559–13569
137.
Zurück zum Zitat Horley GA, Mahon MF, Molloy KC (2002) Synthesis and characterization of novel homoleptic N, N-dialkylcarbamato complexes of antimony: precursors for the deposition of antimony oxides. Inorg Chem 41:5052–5058 Horley GA, Mahon MF, Molloy KC (2002) Synthesis and characterization of novel homoleptic N, N-dialkylcarbamato complexes of antimony: precursors for the deposition of antimony oxides. Inorg Chem 41:5052–5058
138.
Zurück zum Zitat Aresta M, Quaranta E (1988) Reactivity of phosphacarbamates: transfer of the carbamate group promoted by metal assisted electrophilic attack at the carbon dioxide moiety. J Org Chem 53:4153–4154 Aresta M, Quaranta E (1988) Reactivity of phosphacarbamates: transfer of the carbamate group promoted by metal assisted electrophilic attack at the carbon dioxide moiety. J Org Chem 53:4153–4154
139.
Zurück zum Zitat Aresta M, Quaranta E (1992) Alkali-metal-assisted transfer of carbamate group from phosphocarbamates to alkyl halides: a new easy way to alkali-metal carbamates and to carbamate esters. J Chem Soc Dalton Trans 1893–1898 Aresta M, Quaranta E (1992) Alkali-metal-assisted transfer of carbamate group from phosphocarbamates to alkyl halides: a new easy way to alkali-metal carbamates and to carbamate esters. J Chem Soc Dalton Trans 1893–1898
140.
Zurück zum Zitat Yamazaki N, Tomioka T, Higashi F (1975) Trisubstituted ureas and thioureas from hexaalkylphosphorous triamides, primary amines, and carbon dioxide or carbon disulfide. Synthesis 384–385 Yamazaki N, Tomioka T, Higashi F (1975) Trisubstituted ureas and thioureas from hexaalkylphosphorous triamides, primary amines, and carbon dioxide or carbon disulfide. Synthesis 384–385
141.
Zurück zum Zitat Breederveld H (1962) The reaction of dialkylaminosilanes with carbon dioxide and with carbon disulphide. Rec Trav Chim 81:276–278 Breederveld H (1962) The reaction of dialkylaminosilanes with carbon dioxide and with carbon disulphide. Rec Trav Chim 81:276–278
142.
Zurück zum Zitat Cavell RG, Griend LV (1983) Formation and dynamic exchange processes in methyltris(trifluoromethyl)(dimethylcarbamato-O, O′)phosphorus(V). Inorg Chem 22:2066–2070 Cavell RG, Griend LV (1983) Formation and dynamic exchange processes in methyltris(trifluoromethyl)(dimethylcarbamato-O, O′)phosphorus(V). Inorg Chem 22:2066–2070
143.
Zurück zum Zitat Aresta M, Ballivet-Tkatchenko D, Bonnet M (1985) The role of a bifunctional P, N ligand in CO2 coordination. Nouv J Chim 9:321–323 Aresta M, Ballivet-Tkatchenko D, Bonnet M (1985) The role of a bifunctional P, N ligand in CO2 coordination. Nouv J Chim 9:321–323
144.
Zurück zum Zitat Walther D, Gebbardt P, Fischer R, Kreher U, Gorls H (1998) Complexes of the bis(trimethylsilyl)-benzamidinato ligand ‘siam’: synthesis and X-ray structures of (siam)2M, (siam)(siamH)MX (M = Ni, Pd), (siam)2MnI and (siam)ReO3, and their reactivity towards CO2. Inorg Chim Acta 281:181–189 Walther D, Gebbardt P, Fischer R, Kreher U, Gorls H (1998) Complexes of the bis(trimethylsilyl)-benzamidinato ligand ‘siam’: synthesis and X-ray structures of (siam)2M, (siam)(siamH)MX (M = Ni, Pd), (siam)2MnI and (siam)ReO3, and their reactivity towards CO2. Inorg Chim Acta 281:181–189
145.
Zurück zum Zitat Sita LR, Babcock JR, Xi R (1996) Facile metathetical exchange between carbon dioxide and the divalent Group 14 bisamides M[N(SiMe3)2]2 (M = Ge and Sn). J Am Chem Soc 118:10912–10913 Sita LR, Babcock JR, Xi R (1996) Facile metathetical exchange between carbon dioxide and the divalent Group 14 bisamides M[N(SiMe3)2]2 (M = Ge and Sn). J Am Chem Soc 118:10912–10913
146.
Zurück zum Zitat Habereder T, Noth H, Paine RT (2007) Synthesis and reactivity of new bis(tetramethylpiperidino)(phosphanyl)-alumanes. Eur J Inorg Chem 4298–4305 Habereder T, Noth H, Paine RT (2007) Synthesis and reactivity of new bis(tetramethylpiperidino)(phosphanyl)-alumanes. Eur J Inorg Chem 4298–4305
147.
Zurück zum Zitat Bennet MA, Castro J, Edwards AJ, Kopp MR, Wenger E, Willis AC (2001) Preparation and reactivity of nickel(0) complexes with η2-coordinated alkynylphosphines. Organometallics 20:980–989 Bennet MA, Castro J, Edwards AJ, Kopp MR, Wenger E, Willis AC (2001) Preparation and reactivity of nickel(0) complexes with η2-coordinated alkynylphosphines. Organometallics 20:980–989
148.
Zurück zum Zitat Buhro WE, Chisholm MH, Martin JD, Huffmann JC, Folting K, Streib WE (1989) Reactions involving carbon dioxide and mixed amido-phosphido dinuclear compounds: M2(NMe2)4(PR2)(M≡M), where M = Mo and W. Comparative study of the insertion of carbon dioxide into metal-nitrogen and metal-phosphorus bonds. J Am Chem Soc 111:8149–8156 Buhro WE, Chisholm MH, Martin JD, Huffmann JC, Folting K, Streib WE (1989) Reactions involving carbon dioxide and mixed amido-phosphido dinuclear compounds: M2(NMe2)4(PR2)(M≡M), where M = Mo and W. Comparative study of the insertion of carbon dioxide into metal-nitrogen and metal-phosphorus bonds. J Am Chem Soc 111:8149–8156
149.
Zurück zum Zitat Buhro WE, Chisholm MH, Folting K, Huffmann JC (1989) Phosphinecarboxylate ligands formed by insertion of carbon dioxide into metal-phosphido bonds. Preparation and structural characterization of tetrakis(di-tert-butylphosphinecarboxylato)dimolybdenum. Inorg Chem 26:3087–3088 Buhro WE, Chisholm MH, Folting K, Huffmann JC (1989) Phosphinecarboxylate ligands formed by insertion of carbon dioxide into metal-phosphido bonds. Preparation and structural characterization of tetrakis(di-tert-butylphosphinecarboxylato)dimolybdenum. Inorg Chem 26:3087–3088
150.
Zurück zum Zitat Murakami M, Ishida N, Miura T (2006) Solvent and ligand partition reaction pathways in nickel-mediated carboxylation of methylenecyclopropanes. Chem Commun 643–645 Murakami M, Ishida N, Miura T (2006) Solvent and ligand partition reaction pathways in nickel-mediated carboxylation of methylenecyclopropanes. Chem Commun 643–645
151.
Zurück zum Zitat Behr A, Thelen G (1984) Carbon-carbon coupling of carbon dioxide, cyclic hydrocarbon and nickel(0). C1 Mol Chem 1:137–153 Behr A, Thelen G (1984) Carbon-carbon coupling of carbon dioxide, cyclic hydrocarbon and nickel(0). C1 Mol Chem 1:137–153
152.
Zurück zum Zitat Inoue Y, Hibi T, Satake M, Hashimoto H (1979) Reaction of methylenecyclopropanes with carbon dioxide catalysed by palladium(0) complexes. Synthesis of five-membered lactones. J Chem Soc Chem Commun 982–982 Inoue Y, Hibi T, Satake M, Hashimoto H (1979) Reaction of methylenecyclopropanes with carbon dioxide catalysed by palladium(0) complexes. Synthesis of five-membered lactones. J Chem Soc Chem Commun 982–982
153.
Zurück zum Zitat Binger P, Weintz HJ (1984) Reaktionen der methylencyclopropane, VIII1). Palladium(0)-katalysierte darstellung ungesättigter γ-lactone aus methylencyclopropan und kohlendioxid. Chem Ber 117:654–665 Binger P, Weintz HJ (1984) Reaktionen der methylencyclopropane, VIII1). Palladium(0)-katalysierte darstellung ungesättigter γ-lactone aus methylencyclopropan und kohlendioxid. Chem Ber 117:654–665
154.
Zurück zum Zitat Aresta M, Quaranta E, Ciccarese A (1985) Rh(I) promoted activation and fixation of carbon dioxide. C1 Mol Chem 2:267–281 Aresta M, Quaranta E, Ciccarese A (1985) Rh(I) promoted activation and fixation of carbon dioxide. C1 Mol Chem 2:267–281
155.
Zurück zum Zitat Dou XY, He LN, Yang ZZ, Wang JL (2010) Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide. Synlett 14:2159–2163 Dou XY, He LN, Yang ZZ, Wang JL (2010) Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide. Synlett 14:2159–2163
156.
Zurück zum Zitat Phung C, Ulrich RM, Ibrahim M, Tighe NTG, Lieberman DL, Pinhas AR (2011) The solvent-free and catalyst-free conversion of an aziridine to an oxazolidinone using only carbon dioxide. Green Chem 13:3224–3229 Phung C, Ulrich RM, Ibrahim M, Tighe NTG, Lieberman DL, Pinhas AR (2011) The solvent-free and catalyst-free conversion of an aziridine to an oxazolidinone using only carbon dioxide. Green Chem 13:3224–3229
157.
Zurück zum Zitat Hancock MT, Pinhas AL (2003) A convenient and inexpensive conversion of an aziridine to an oxazolidinone. Tetrahedron Lett 44:5457–5460 Hancock MT, Pinhas AL (2003) A convenient and inexpensive conversion of an aziridine to an oxazolidinone. Tetrahedron Lett 44:5457–5460
158.
Zurück zum Zitat Du Y, Wu Y, Liu AH, He LN (2008) Quaternary ammonium bromide functionalized polyethylene glycol: a high efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions. J Org Chem 73:4709–4712 Du Y, Wu Y, Liu AH, He LN (2008) Quaternary ammonium bromide functionalized polyethylene glycol: a high efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions. J Org Chem 73:4709–4712
159.
Zurück zum Zitat Yang ZZ, He LN, Peng SY, Liu AH (2010) Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions. Green Chem 12:1850–1854 Yang ZZ, He LN, Peng SY, Liu AH (2010) Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions. Green Chem 12:1850–1854
160.
Zurück zum Zitat Mu WH, Chasse GQ, Fang DC (2008) High level ab initio exploration on the conversion of carbon dioxide into oxazolidinones: the mechanism and regioselectivity. J Chem Phys A 112:6708–6714 Mu WH, Chasse GQ, Fang DC (2008) High level ab initio exploration on the conversion of carbon dioxide into oxazolidinones: the mechanism and regioselectivity. J Chem Phys A 112:6708–6714
161.
Zurück zum Zitat Sudo A, Morioka Y, Sanda F, Endo T (2004) N-Tosyl aziridine, a new substrate for chemical fixation of carbon dioxide via ring expansion reaction under atmospheric pressure. Tetrahedron Lett 45:1363–1365 Sudo A, Morioka Y, Sanda F, Endo T (2004) N-Tosyl aziridine, a new substrate for chemical fixation of carbon dioxide via ring expansion reaction under atmospheric pressure. Tetrahedron Lett 45:1363–1365
162.
Zurück zum Zitat Wu Y, Liu G (2011) Organocatalyzed cycloaddition of carbon dioxide to aziridines. Tetrahedron Lett 52:6450–6452 Wu Y, Liu G (2011) Organocatalyzed cycloaddition of carbon dioxide to aziridines. Tetrahedron Lett 52:6450–6452
163.
Zurück zum Zitat Phung C, Pinhas AR (2010) The high yield and regioselective conversion of an unactivated aziridine to an oxazolidinone using carbon dioxide with ammonium iodide as the catalyst. Tetrahedron Lett 51:4552–4554 Phung C, Pinhas AR (2010) The high yield and regioselective conversion of an unactivated aziridine to an oxazolidinone using carbon dioxide with ammonium iodide as the catalyst. Tetrahedron Lett 51:4552–4554
164.
Zurück zum Zitat Miller AW, Nguyen SB (2004) (Salen)chromium (III)/DMAP: an efficient catalyst system for the selective synthesis of 5-substituted oxazolidinones from carbon dioxide and aziridines. Org Lett 6:2301–2304 Miller AW, Nguyen SB (2004) (Salen)chromium (III)/DMAP: an efficient catalyst system for the selective synthesis of 5-substituted oxazolidinones from carbon dioxide and aziridines. Org Lett 6:2301–2304
165.
Zurück zum Zitat Wu Y, He LN, Du Y, Wang JQ, Miao CX, Li W (2009) Zirconyl chloride: an efficient recyclable catalyst for synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions. Tetrahedron 65:6204–6210 Wu Y, He LN, Du Y, Wang JQ, Miao CX, Li W (2009) Zirconyl chloride: an efficient recyclable catalyst for synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions. Tetrahedron 65:6204–6210
166.
Zurück zum Zitat Watile RA, Bagal DB, Patil YP, Bhanage BM (2011) Regioselective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines using Br-Ph3 +PPEG600P+Ph3Br- as an efficient, homogenous recyclable catalyst at ambient conditions. Tetrahedron Lett 52:6383–6387 Watile RA, Bagal DB, Patil YP, Bhanage BM (2011) Regioselective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines using Br-Ph3 +PPEG600P+Ph3Br- as an efficient, homogenous recyclable catalyst at ambient conditions. Tetrahedron Lett 52:6383–6387
167.
Zurück zum Zitat Watile RA, Bagal DB, Deshmukh KM, Dhake KP, Bhanage BM (2011) Polymer supported diol functionalized ionic liquids: an efficient, heterogeneous and recyclable catalyst for 5-aryl-2-oxazolidinones synthesis from CO2 and aziridines under mild and solvent free conditions. J Mol Catal A 351:196–203 Watile RA, Bagal DB, Deshmukh KM, Dhake KP, Bhanage BM (2011) Polymer supported diol functionalized ionic liquids: an efficient, heterogeneous and recyclable catalyst for 5-aryl-2-oxazolidinones synthesis from CO2 and aziridines under mild and solvent free conditions. J Mol Catal A 351:196–203
168.
Zurück zum Zitat Jiang HF, Ye JW, Qi CR, Huang LB (2010) Naturally occurring α-amino acid: a simple and inexpensive catalyst for the selective synthesis of 5-aryl-2-oxazolidinones from CO2 and aziridines under solvent-free conditions. Tetrahedron Lett 51:928–932 Jiang HF, Ye JW, Qi CR, Huang LB (2010) Naturally occurring α-amino acid: a simple and inexpensive catalyst for the selective synthesis of 5-aryl-2-oxazolidinones from CO2 and aziridines under solvent-free conditions. Tetrahedron Lett 51:928–932
169.
Zurück zum Zitat Qi C, Ye J, Zeng W, Jiang H (2010) Polystyrene-supported amino acids as efficient catalyst for chemical fixation of carbon dioxide. Adv Synth Catal 352:1925–1933 Qi C, Ye J, Zeng W, Jiang H (2010) Polystyrene-supported amino acids as efficient catalyst for chemical fixation of carbon dioxide. Adv Synth Catal 352:1925–1933
170.
Zurück zum Zitat Soga K, Hosoda S, Nakamura H, Ikeda S (1976) A new synthetic route to 2-oxazolidones. J Chem Soc Chem Commun 617–617 Soga K, Hosoda S, Nakamura H, Ikeda S (1976) A new synthetic route to 2-oxazolidones. J Chem Soc Chem Commun 617–617
171.
Zurück zum Zitat Kawanami H, Ikushima Y (2002) Regioselectivity and selective enhancement of carbon dioxide fixation of 2-substituted aziridines to 2-oxazolidinones under supercritical conditions. Tetrahedron Lett 43:3841–3844 Kawanami H, Ikushima Y (2002) Regioselectivity and selective enhancement of carbon dioxide fixation of 2-substituted aziridines to 2-oxazolidinones under supercritical conditions. Tetrahedron Lett 43:3841–3844
172.
Zurück zum Zitat Zhou H, Wang YM, Zhang WZ, Qu JP, Lu XB (2011) N-Heterocyclic carbene functionalized MCM-41 as an efficient catalyst for chemical fixation of carbon dioxide. Green Chem 13:644–650 Zhou H, Wang YM, Zhang WZ, Qu JP, Lu XB (2011) N-Heterocyclic carbene functionalized MCM-41 as an efficient catalyst for chemical fixation of carbon dioxide. Green Chem 13:644–650
173.
Zurück zum Zitat Tascedda P, Duñach R (2000) Electrosynthesis of cyclic carbamates from aziridines and carbon dioxide. Chem Commun 449–450 Tascedda P, Duñach R (2000) Electrosynthesis of cyclic carbamates from aziridines and carbon dioxide. Chem Commun 449–450
174.
Zurück zum Zitat Fontana F, Chen CC, Aggarwal V (2011) Palladium-catalyzed insertion of CO2 into vinylaziridines: new route to 5-vinyloxazolidinones. Org Lett 13:3454–3457 Fontana F, Chen CC, Aggarwal V (2011) Palladium-catalyzed insertion of CO2 into vinylaziridines: new route to 5-vinyloxazolidinones. Org Lett 13:3454–3457
175.
Zurück zum Zitat Ihata O, Kayaki Y, Ikariya T (2005) Aliphatic poly(urethane-amine)s synthesized by copolymerization of aziridines and supercritical carbon dioxide. Macromolecules 38:6429–6434 Ihata O, Kayaki Y, Ikariya T (2005) Aliphatic poly(urethane-amine)s synthesized by copolymerization of aziridines and supercritical carbon dioxide. Macromolecules 38:6429–6434
176.
Zurück zum Zitat Pinkes JR, Steffey BD, Vites JC, Cutler AR (1994) Carbon dioxide insertion into the iron-zirconium and ruthenium-zirconium bonds of the heterobimetallic complexes Cp(CO)2MZr(Cl)Cp2: direct production of the μ-η1(C):η2(O, O′)-CO2 compounds Cp(CO)2MCO2Zr(Cl)Cp2. Organometallics 13(1):21–23 Pinkes JR, Steffey BD, Vites JC, Cutler AR (1994) Carbon dioxide insertion into the iron-zirconium and ruthenium-zirconium bonds of the heterobimetallic complexes Cp(CO)2MZr(Cl)Cp2: direct production of the μ-η1(C):η2(O, O′)-CO2 compounds Cp(CO)2MCO2Zr(Cl)Cp2. Organometallics 13(1):21–23
177.
Zurück zum Zitat Riduan SN, Zhang Y (2010) Recent developments in carbon dioxide utilization under mild conditions. Dalton Trans 39:3347–3357 Riduan SN, Zhang Y (2010) Recent developments in carbon dioxide utilization under mild conditions. Dalton Trans 39:3347–3357
179.
Zurück zum Zitat Song JJ, Gallou F, Reeves JT, Tan Z, Yee NK, Senanayake CH (2006) Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds. J Org Chem 71:1273–1276 Song JJ, Gallou F, Reeves JT, Tan Z, Yee NK, Senanayake CH (2006) Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds. J Org Chem 71:1273–1276
180.
Zurück zum Zitat Suzuki Y, Bakar A, Muramatsu K, Sato M (2006) Cyanosilylation of aldehydes catalyzed by N-heterocyclic carbenes. Tetrahedron 62:4227–4231 Suzuki Y, Bakar A, Muramatsu K, Sato M (2006) Cyanosilylation of aldehydes catalyzed by N-heterocyclic carbenes. Tetrahedron 62:4227–4231
181.
Zurück zum Zitat Kolbe H (1860) Ueber Synthese der Salicylsäure. Just Lieb Ann Chem 113:125–127 Kolbe H (1860) Ueber Synthese der Salicylsäure. Just Lieb Ann Chem 113:125–127
182.
Zurück zum Zitat Schmitt R, Burkard E (1877) Ueber Naphtolcarbonsäuren. Chem Ber 20:2699–1702 Schmitt R, Burkard E (1877) Ueber Naphtolcarbonsäuren. Chem Ber 20:2699–1702
183.
Zurück zum Zitat Dinjus E, Leitner W (1995) New insights into the palladium-catalysed synthesis of δ-lactones from 1,3-dienes and carbon dioxide. Appl Organomet Chem 9(1):43–50 Dinjus E, Leitner W (1995) New insights into the palladium-catalysed synthesis of δ-lactones from 1,3-dienes and carbon dioxide. Appl Organomet Chem 9(1):43–50
184.
Zurück zum Zitat Aresta M, Tommasi I, Dileo C, Dibenedetto A, Narracci M, Ziolkowski J, Jezierski A (2001) Synthesis and spectroscopic (1H NMR, ESR) characterization of new aryloxy-Mn(II) complexes: steric control over O- vs. phenyl-π-coordination of ArO-ligands (ArO-=C6H5O-, 4-methyl-C6H4O-, 3,5-dimethyl-C6H3O-, 2,6-di-tert-butyl-C6H3O-, 2,6-dimethyl-C6H3O-) to the “Mn(II)Cp” moiety, and their reactivity with carbon dioxide. Can J Chem 79(5–6):570–577 Aresta M, Tommasi I, Dileo C, Dibenedetto A, Narracci M, Ziolkowski J, Jezierski A (2001) Synthesis and spectroscopic (1H NMR, ESR) characterization of new aryloxy-Mn(II) complexes: steric control over O- vs. phenyl-π-coordination of ArO-ligands (ArO-=C6H5O-, 4-methyl-C6H4O-, 3,5-dimethyl-C6H3O-, 2,6-di-tert-butyl-C6H3O-, 2,6-dimethyl-C6H3O-) to the “Mn(II)Cp” moiety, and their reactivity with carbon dioxide. Can J Chem 79(5–6):570–577
186.
Zurück zum Zitat Aresta M, Tkatchenko I, Tommasi I (2003) In: Rogers RD, Seddon KR (eds) Ionic liquids as green solvents: progress and prospects, vol 856, ACS Symposium Series. ACS, Washington DC, p 93 Aresta M, Tkatchenko I, Tommasi I (2003) In: Rogers RD, Seddon KR (eds) Ionic liquids as green solvents: progress and prospects, vol 856, ACS Symposium Series. ACS, Washington DC, p 93
187.
Zurück zum Zitat Barran T, Dibenedetto A, Aresta M, Kruczała K, Macyk W (2014) Photocatalytic carboxylation of organic substrates with carbon dioxide at zinc sulfide with deposited ruthenium nanoparticles. ChemPlusChem 79:708–715 Barran T, Dibenedetto A, Aresta M, Kruczała K, Macyk W (2014) Photocatalytic carboxylation of organic substrates with carbon dioxide at zinc sulfide with deposited ruthenium nanoparticles. ChemPlusChem 79:708–715
Metadaten
Titel
Insertion of CO2 into E–X Bonds
verfasst von
Michele Aresta
Angela Dibenedetto
Eugenio Quaranta
Copyright-Jahr
2016
Verlag
Springer Berlin Heidelberg
DOI
https://doi.org/10.1007/978-3-662-46831-9_4

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.