Skip to main content
Erschienen in: Topics in Catalysis 18-19/2018

06.07.2018 | Original Paper

Cobalt-Catalyzed Green Cross-Dehydrogenative C(sp2)-H/P-H Coupling Reactions

verfasst von: Mikhail Khrizanforov, Sofia Strekalova, Vera Khrizanforova, Alexey Dobrynin, Kirill Kholin, Tatyana Gryaznova, Valeriya Grinenko, Aidar Gubaidullin, M. K. Kadirov, Yulia Budnikova

Erschienen in: Topics in Catalysis | Ausgabe 18-19/2018

Einloggen

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

search-config
loading …

Abstract

Joined electrolysis of arenes (benzene or coumarin derivatives) and diethyl-H-phosphonate (EtO)2P(O)H in the presence of [CoCl2(bpy)] catalyst (5%) in an ethanol-aqueous solution in reductive conditions allows obtaining the desired products in a single step by aromatic C–H bonds phosphonation with yields up to 70%. The only by-product is hydrogen; the reaction proceeds at room temperature and does not require specially added reducing agents and oxidants or other initiators. Radical mechanism has been confirmed for the catalytic reaction proceeding via bicobalt phosphonates with Co–P bond, the structure of which also has been identified.

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!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, Leazer Jr JL, Linderman LK, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY (2007) Key green chemistry research areas—a perspective from pharmaceutical manufacturers. Green Chem 9:411–420 Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, Leazer Jr JL, Linderman LK, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY (2007) Key green chemistry research areas—a perspective from pharmaceutical manufacturers. Green Chem 9:411–420
2.
Zurück zum Zitat Fabry DC, Rueping M (2016) Merging visible light photoredox catalysis with metal catalyzed C–H activations: on the role of oxygen and superoxide ions as oxidants. Acc Chem Res 49:1969–1979PubMedPubMedCentral Fabry DC, Rueping M (2016) Merging visible light photoredox catalysis with metal catalyzed C–H activations: on the role of oxygen and superoxide ions as oxidants. Acc Chem Res 49:1969–1979PubMedPubMedCentral
3.
Zurück zum Zitat Chupakhin ON, Charushin VN (2016) Recent advances in the field of nucleophilic aromatic substitution of hydrogen. Tetrahedron Lett 57:2665–2672 Chupakhin ON, Charushin VN (2016) Recent advances in the field of nucleophilic aromatic substitution of hydrogen. Tetrahedron Lett 57:2665–2672
4.
Zurück zum Zitat Rodesly F, Oble J, Poli G (2017) Metal-catalyzed CH activation/functionalization: the fundamentals. J Mol Catal A 426:275–296 Rodesly F, Oble J, Poli G (2017) Metal-catalyzed CH activation/functionalization: the fundamentals. J Mol Catal A 426:275–296
5.
Zurück zum Zitat Budnikova YH, Sinyashin OG (2015) Phosphorylation of C–H bonds of aromatic compounds using metals and metal complexes. Russ Chem Rev 84:917–951 Budnikova YH, Sinyashin OG (2015) Phosphorylation of C–H bonds of aromatic compounds using metals and metal complexes. Russ Chem Rev 84:917–951
6.
Zurück zum Zitat Mikhaylov DY, Budnikova YH (2013) Fluoroalkylation of organic compounds. Russ Chem Rev 82:835–864 Mikhaylov DY, Budnikova YH (2013) Fluoroalkylation of organic compounds. Russ Chem Rev 82:835–864
7.
Zurück zum Zitat Odinets IL, Vinogradova NM, Lyssenko KA, Petrovskii PV, Mastryukova TA, Röschenthaler GV (2006) Diastereoselective cycloalkylation of phosphoryl and thiophosphoryl acetonitriles by α, ψ-dihalogenalkanes under phase transfer catalysis conditions. Heteroat Chem 17:13–21 Odinets IL, Vinogradova NM, Lyssenko KA, Petrovskii PV, Mastryukova TA, Röschenthaler GV (2006) Diastereoselective cycloalkylation of phosphoryl and thiophosphoryl acetonitriles by α, ψ-dihalogenalkanes under phase transfer catalysis conditions. Heteroat Chem 17:13–21
8.
Zurück zum Zitat Trofimov BA, Arbuzova SN, Gusarova NK (1999) Phosphine in the synthesis of organophosphorus compounds. Russ Chem Rev 68:215–228 Trofimov BA, Arbuzova SN, Gusarova NK (1999) Phosphine in the synthesis of organophosphorus compounds. Russ Chem Rev 68:215–228
9.
Zurück zum Zitat Lebel H, Morin S, Paquet V (2003) Alkylation of phosphine boranes by phase-transfer catalysis. Org Lett 5:2347–2349PubMed Lebel H, Morin S, Paquet V (2003) Alkylation of phosphine boranes by phase-transfer catalysis. Org Lett 5:2347–2349PubMed
10.
Zurück zum Zitat Odinets IL, Matveeva EV (2012) The application of green chemistry methods in organophosphorus synthesis. Russ Chem Rev 81:221–238 Odinets IL, Matveeva EV (2012) The application of green chemistry methods in organophosphorus synthesis. Russ Chem Rev 81:221–238
11.
Zurück zum Zitat Budnikova YH, Gryaznova TV, Grinenko VV, Dudkina YB, Khrizanforov MN (2017) Eco-efficient electrocatalytic C–P bond formation. Pure Appl Chem 89:311–330 Budnikova YH, Gryaznova TV, Grinenko VV, Dudkina YB, Khrizanforov MN (2017) Eco-efficient electrocatalytic C–P bond formation. Pure Appl Chem 89:311–330
12.
Zurück zum Zitat Budnikova YH, Krasnov SA, Gryaznova TV, Tomilov AP, Turigin VV, Magdeev IM, Sinyashin OG (2008) “Green” ways of phosphorus compounds preparation. Phosphorus Sulfur Silicon Relat Elem 183:513–518 Budnikova YH, Krasnov SA, Gryaznova TV, Tomilov AP, Turigin VV, Magdeev IM, Sinyashin OG (2008) “Green” ways of phosphorus compounds preparation. Phosphorus Sulfur Silicon Relat Elem 183:513–518
13.
Zurück zum Zitat Budnikova YH, Yakhvarov DG, Sinyashin OG (2005) Electrocatalytic eco-efficient functionalization of white phosphorus. J Organomet Chem 690:2416–2425 Budnikova YH, Yakhvarov DG, Sinyashin OG (2005) Electrocatalytic eco-efficient functionalization of white phosphorus. J Organomet Chem 690:2416–2425
14.
Zurück zum Zitat Li C-J (2016) Exploration of new chemical reactivities for sustainable molecular transformations. Chem 1(3):423–437 Li C-J (2016) Exploration of new chemical reactivities for sustainable molecular transformations. Chem 1(3):423–437
15.
Zurück zum Zitat Feng C-G, Ye M, Xiao K-J, Li S, Yu J-Q (2013) Pd(II)-catalyzed phosphorylation of aryl C–H bonds. J Am Chem Soc 135(25):9322–9325PubMed Feng C-G, Ye M, Xiao K-J, Li S, Yu J-Q (2013) Pd(II)-catalyzed phosphorylation of aryl C–H bonds. J Am Chem Soc 135(25):9322–9325PubMed
16.
Zurück zum Zitat Chen P, Sun Y, Wu Y, Liu L, Zhu J, Zhao Y (2017) A theoretical study on the mechanism of ruthenium(II)-catalyzed phosphoryl-directed ortho-selective C–H bond activations: the phosphoryl hydroxy group triggered Ru(II)/Ru(0) catalytic cycle. Org Chem Front 4:1482–1492 Chen P, Sun Y, Wu Y, Liu L, Zhu J, Zhao Y (2017) A theoretical study on the mechanism of ruthenium(II)-catalyzed phosphoryl-directed ortho-selective C–H bond activations: the phosphoryl hydroxy group triggered Ru(II)/Ru(0) catalytic cycle. Org Chem Front 4:1482–1492
17.
Zurück zum Zitat Liu L, Yuan H, Fu T, Wang T, Gao X, Zeng Z, Zhu J, Zhao Y (2014) Double role of the hydroxy group of phosphoryl in palladium(II)-catalyzed ortho-olefination: a combined experimental and theoretical investigation. J Org Chem 79(1):80–87PubMed Liu L, Yuan H, Fu T, Wang T, Gao X, Zeng Z, Zhu J, Zhao Y (2014) Double role of the hydroxy group of phosphoryl in palladium(II)-catalyzed ortho-olefination: a combined experimental and theoretical investigation. J Org Chem 79(1):80–87PubMed
18.
Zurück zum Zitat Kosolapoff GM, Maier L (1972) Organic phosphorus compounds. Wiley, New York Kosolapoff GM, Maier L (1972) Organic phosphorus compounds. Wiley, New York
19.
Zurück zum Zitat Corbridge DEC (2013) Phosphorus: chemistry, biochemistry and technology. CRC Press, London Corbridge DEC (2013) Phosphorus: chemistry, biochemistry and technology. CRC Press, London
20.
Zurück zum Zitat Swaminathan S, Narayanan KV (1971) Rupe and meyer-schuster rearrangements. Chem Rev 71:429–438 Swaminathan S, Narayanan KV (1971) Rupe and meyer-schuster rearrangements. Chem Rev 71:429–438
21.
Zurück zum Zitat Bhattacharya AK, Thyagarajan G (1981) Michaelis-arbuzov rearrangement. Chem Rev 81:415–430 Bhattacharya AK, Thyagarajan G (1981) Michaelis-arbuzov rearrangement. Chem Rev 81:415–430
22.
Zurück zum Zitat Kostova I (2005) Synthetic and natural coumarins as cytotoxic agents. Curr Med Chem 5:29–46 Kostova I (2005) Synthetic and natural coumarins as cytotoxic agents. Curr Med Chem 5:29–46
23.
Zurück zum Zitat Venugopala KN, Rashmi V, Odhav B (2013) Review on natural coumarin lead compounds for their pharmacological activity. Biomed Res Int 2013:1–14 Venugopala KN, Rashmi V, Odhav B (2013) Review on natural coumarin lead compounds for their pharmacological activity. Biomed Res Int 2013:1–14
24.
Zurück zum Zitat Budzisz E, Brzezinska E, Krajewska U, Rozalski M (2003) Cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues. Eur J Med Chem 38:597–603PubMed Budzisz E, Brzezinska E, Krajewska U, Rozalski M (2003) Cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues. Eur J Med Chem 38:597–603PubMed
25.
Zurück zum Zitat Engel R, Cohen JI (2003) Synthesis of carbon–phosphorus bonds. CRC Press, Boca Raton Engel R, Cohen JI (2003) Synthesis of carbon–phosphorus bonds. CRC Press, Boca Raton
26.
Zurück zum Zitat Tavs P (1970) Reaktion von Arylhalogeniden mit Trialkylphosphiten und Benzolphosphonigsäure-dialkylestern zu aromatischen Phosphonsäureestern und Phosphinsäureestern unter Nickelsalzkatalyse. Eur J Inorg Chem 103:2428–2436 Tavs P (1970) Reaktion von Arylhalogeniden mit Trialkylphosphiten und Benzolphosphonigsäure-dialkylestern zu aromatischen Phosphonsäureestern und Phosphinsäureestern unter Nickelsalzkatalyse. Eur J Inorg Chem 103:2428–2436
27.
Zurück zum Zitat Connor JA, Jones AC, Price R (1980) Copper (II) ethanoate-assisted phosphonation of aryl halides. J Chem Soc Chem Commun 4:137–138 Connor JA, Jones AC, Price R (1980) Copper (II) ethanoate-assisted phosphonation of aryl halides. J Chem Soc Chem Commun 4:137–138
28.
Zurück zum Zitat Hall N, Price R (1979) The copper-promoted reaction of o-halogenodiarylazo-compounds with nucleophiles. Part 1. The copper-promoted reaction of o-bromodiarylazo-compounds with trialkyl phosphites. A novel method for the preparation of dialkyl arylphosphonates. J Chem Soc Perkin Trans 1:2634–2641 Hall N, Price R (1979) The copper-promoted reaction of o-halogenodiarylazo-compounds with nucleophiles. Part 1. The copper-promoted reaction of o-bromodiarylazo-compounds with trialkyl phosphites. A novel method for the preparation of dialkyl arylphosphonates. J Chem Soc Perkin Trans 1:2634–2641
29.
Zurück zum Zitat Hirao T, Masunaga T, Oshiro Y, Agawa T (1981) A novel synthesis of dialkyl arenephosphonates. Synthesis 1981:56–57 Hirao T, Masunaga T, Oshiro Y, Agawa T (1981) A novel synthesis of dialkyl arenephosphonates. Synthesis 1981:56–57
30.
Zurück zum Zitat Hirao T, Masunaga T, Yamada N, Oshiro Y, Agawa T (1982) Palladium-catalyzed new carbon-phosphorus bond formation. Bull Chem Soc Jpn 55:909–913 Hirao T, Masunaga T, Yamada N, Oshiro Y, Agawa T (1982) Palladium-catalyzed new carbon-phosphorus bond formation. Bull Chem Soc Jpn 55:909–913
31.
Zurück zum Zitat Battagia S, Vyle S (2003) Novel methodology for the preparation and purification of oligonucleotides incorporating phosphorothiolate termini. Tetrahedron Lett 44:861–863 Battagia S, Vyle S (2003) Novel methodology for the preparation and purification of oligonucleotides incorporating phosphorothiolate termini. Tetrahedron Lett 44:861–863
32.
Zurück zum Zitat Obrycki R, Griffin CE (1968) Phosphonic acids and esters. XIX. Synthesis of substituted phenyl-and arylphosphonates by the photoinitiated arylation of trialkyl phosphites. J Org Chem 33:632–636 Obrycki R, Griffin CE (1968) Phosphonic acids and esters. XIX. Synthesis of substituted phenyl-and arylphosphonates by the photoinitiated arylation of trialkyl phosphites. J Org Chem 33:632–636
33.
Zurück zum Zitat Bunnett JF, Creary X (1974) Photostimulated condensation of aryl iodides with potassium dialkyl phosphites to form dialkyl arylphosphonates. J Org Chem 39:3612–3614 Bunnett JF, Creary X (1974) Photostimulated condensation of aryl iodides with potassium dialkyl phosphites to form dialkyl arylphosphonates. J Org Chem 39:3612–3614
34.
Zurück zum Zitat Jason EF, Fields EK (1962) Free-radical phosphonation of aromatic compounds. J Org Chem 27:1402–1405 Jason EF, Fields EK (1962) Free-radical phosphonation of aromatic compounds. J Org Chem 27:1402–1405
35.
Zurück zum Zitat Kottman H, Skarzewski J, Effenberger F (1987) Oxidative phosphonylierung von aromaten mit cerammoniumnitrat. Synthesis 1987:797–801 Kottman H, Skarzewski J, Effenberger F (1987) Oxidative phosphonylierung von aromaten mit cerammoniumnitrat. Synthesis 1987:797–801
36.
Zurück zum Zitat Effenberger F, Kottmann H (1985) Oxidative phosphonylation of aromatic compounds. Tetrahedron 41:4171–4182 Effenberger F, Kottmann H (1985) Oxidative phosphonylation of aromatic compounds. Tetrahedron 41:4171–4182
37.
Zurück zum Zitat Kagayama T, Nakano A, Sakaguchi S, Ishii Y (2006) Phosphonation of arenes with dialkyl phosphites catalyzed by Mn (II)/Co (II)/O2 redox couple. Org Lett 8:407–409PubMed Kagayama T, Nakano A, Sakaguchi S, Ishii Y (2006) Phosphonation of arenes with dialkyl phosphites catalyzed by Mn (II)/Co (II)/O2 redox couple. Org Lett 8:407–409PubMed
38.
Zurück zum Zitat Mao X, Ma X, Zhang S, Hu H, Zhu C, Cheng Y (2013) Silver-catalyzed highly regioselective phosphonation of arenes bearing electron-withdrawing groups. Eur J Org Chem 20:4245–4248 Mao X, Ma X, Zhang S, Hu H, Zhu C, Cheng Y (2013) Silver-catalyzed highly regioselective phosphonation of arenes bearing electron-withdrawing groups. Eur J Org Chem 20:4245–4248
39.
Zurück zum Zitat Ohmori H, Nakai S, Masui M (1979) Anodic oxidation of organophosphorus compounds. Part 2. Formation of dialkyl arylphosphonates via arylation of trialkyl phosphites. J Chem Soc Perkin Trans 1:2023–2026 Ohmori H, Nakai S, Masui M (1979) Anodic oxidation of organophosphorus compounds. Part 2. Formation of dialkyl arylphosphonates via arylation of trialkyl phosphites. J Chem Soc Perkin Trans 1:2023–2026
40.
Zurück zum Zitat Nikitin EV, Romakhin AS, Parakin OV, Romanov GV, Kargin YM, Pudovik AN (1983) Electrochemical synthesis of aryl phosphonates. Russ Chem Bull 32:566–569 Nikitin EV, Romakhin AS, Parakin OV, Romanov GV, Kargin YM, Pudovik AN (1983) Electrochemical synthesis of aryl phosphonates. Russ Chem Bull 32:566–569
41.
Zurück zum Zitat Cruz H, Gallardo I, Guirado G (2011) Electrochemical synthesis of organophosphorus compounds through nucleophilic aromatic substitution: mechanistic investigations and synthetic scope. Eur J Org Chem 36:7378–7389 Cruz H, Gallardo I, Guirado G (2011) Electrochemical synthesis of organophosphorus compounds through nucleophilic aromatic substitution: mechanistic investigations and synthetic scope. Eur J Org Chem 36:7378–7389
42.
Zurück zum Zitat Khrizanforov MN, Strekalova SO, Kholin KV, Khrizanforova VV, Kadirov MK, Gryaznova TV, Budnikova YH (2017) Novel approach to metal-induced oxidative phosphorylation of aromatic compounds. Catal Today 279:133–141 Khrizanforov MN, Strekalova SO, Kholin KV, Khrizanforova VV, Kadirov MK, Gryaznova TV, Budnikova YH (2017) Novel approach to metal-induced oxidative phosphorylation of aromatic compounds. Catal Today 279:133–141
43.
Zurück zum Zitat Robison CN, Addison JF (1966) Condensation of triethyl phosphonoacetate with aromatic aldehydes. J Org Chem 31:4325–4326 Robison CN, Addison JF (1966) Condensation of triethyl phosphonoacetate with aromatic aldehydes. J Org Chem 31:4325–4326
44.
Zurück zum Zitat Singh RK, Rogers MD (1985) An efficient synthesis of diethyl coumarin-3-phosphonates. J Heterocycl Chem 22:1713–1714 Singh RK, Rogers MD (1985) An efficient synthesis of diethyl coumarin-3-phosphonates. J Heterocycl Chem 22:1713–1714
45.
Zurück zum Zitat Bouyssou P, Chenault J (1991) Phosphonates and phosphine oxides as reagents in a one-pot synthesis of coumarins. Tetrahedron Lett 32:5341–5344 Bouyssou P, Chenault J (1991) Phosphonates and phosphine oxides as reagents in a one-pot synthesis of coumarins. Tetrahedron Lett 32:5341–5344
46.
Zurück zum Zitat Rodios NA, Bojilova A, Terzis A, Raptopoulou CP (1994) Reaction of 3-nitro-and 3-diethylphosphonocoumarin with phenacyl bromide. X-ray molecular structure of 3-nitro-3, 4-phenacylidenecoumarin. J Heterocycl Chem 31:1129–1133 Rodios NA, Bojilova A, Terzis A, Raptopoulou CP (1994) Reaction of 3-nitro-and 3-diethylphosphonocoumarin with phenacyl bromide. X-ray molecular structure of 3-nitro-3, 4-phenacylidenecoumarin. J Heterocycl Chem 31:1129–1133
47.
Zurück zum Zitat Bojilova A, Nikolova R, Ivanov C, Rodios NA, Terzis A, Raptopoulou CP (1996) A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1, 2-benzoxaphosphorines and their dimers. Tetrahedron 52:12597–12612 Bojilova A, Nikolova R, Ivanov C, Rodios NA, Terzis A, Raptopoulou CP (1996) A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1, 2-benzoxaphosphorines and their dimers. Tetrahedron 52:12597–12612
48.
Zurück zum Zitat Kostka K, Pastuszko S, Kotynski A, Budzisz E (1998) 4-Derivatives coumarin-3-phosphonic acids and esters. Phosphorus Sulfur Silicon Relat Elem 134:199–209 Kostka K, Pastuszko S, Kotynski A, Budzisz E (1998) 4-Derivatives coumarin-3-phosphonic acids and esters. Phosphorus Sulfur Silicon Relat Elem 134:199–209
49.
Zurück zum Zitat Takeuchi Y, Ueda N, Uesugi K, Abe H, Nishioka H, Harayama T (2003) Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. IV: improved synthetic method of substituted coumarins. Heterocycles 59:217–224 Takeuchi Y, Ueda N, Uesugi K, Abe H, Nishioka H, Harayama T (2003) Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. IV: improved synthetic method of substituted coumarins. Heterocycles 59:217–224
50.
Zurück zum Zitat Zhou P, Jiang YJ, Zou JP, Zhang W (2012) Manganese (III) acetate mediated free-radical phosphonylation of flavones and coumarins. Synthesis 44:1043–1050 Zhou P, Jiang YJ, Zou JP, Zhang W (2012) Manganese (III) acetate mediated free-radical phosphonylation of flavones and coumarins. Synthesis 44:1043–1050
51.
Zurück zum Zitat Mi X, Huang M, Zhang J, Wang C, Wu Y (2013) Regioselective palladium-catalyzed phosphonation of coumarins with dialkyl H-phosphonates via C–H functionalization. Org Lett 15:6266–6269PubMed Mi X, Huang M, Zhang J, Wang C, Wu Y (2013) Regioselective palladium-catalyzed phosphonation of coumarins with dialkyl H-phosphonates via C–H functionalization. Org Lett 15:6266–6269PubMed
52.
Zurück zum Zitat Yuan JW, Li YZ, Yang LR, Mai WP, Mao P, Xiao YM, Qu LB (2015) Silver-catalyzed direct Csp2-H radical phosphorylation of coumarins with H-phosphites. Tetrahedron 71:8178–8186 Yuan JW, Li YZ, Yang LR, Mai WP, Mao P, Xiao YM, Qu LB (2015) Silver-catalyzed direct Csp2-H radical phosphorylation of coumarins with H-phosphites. Tetrahedron 71:8178–8186
53.
Zurück zum Zitat Gao Y, Tang G, Zhao Y (2017) Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations, phosphorus, sulfur, and silicon and the related elements. Phosphorus Sulfur Silicon Relat Elem 192(6):589–596 Gao Y, Tang G, Zhao Y (2017) Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations, phosphorus, sulfur, and silicon and the related elements. Phosphorus Sulfur Silicon Relat Elem 192(6):589–596
54.
Zurück zum Zitat Dudkina YB, Gryaznova TV, Sinyashin OG, Budnikova YH (2015) Ligand-directed electrochemical functionalization of C (sp 2)—H bonds in the presence of the palladium and nickel compounds. Russ Chem Bull 64:1713–1725 Dudkina YB, Gryaznova TV, Sinyashin OG, Budnikova YH (2015) Ligand-directed electrochemical functionalization of C (sp 2)—H bonds in the presence of the palladium and nickel compounds. Russ Chem Bull 64:1713–1725
55.
Zurück zum Zitat Gryaznova T, Dudkina Y, Khrizanforov M, Sinyashin O, Kataeva O, Budnikova Y (2015) Electrochemical properties of diphosphonate-bridged palladacycles and their reactivity in arene phosphonation. J Solid State Electrochem 19:2665–2672 Gryaznova T, Dudkina Y, Khrizanforov M, Sinyashin O, Kataeva O, Budnikova Y (2015) Electrochemical properties of diphosphonate-bridged palladacycles and their reactivity in arene phosphonation. J Solid State Electrochem 19:2665–2672
56.
Zurück zum Zitat Gryaznova TV, Dudkina YB, Islamov DR, Kataeva ON, Sinyashin OG, Vicic DA, Budnikova Y (2015) Pyridine-directed palladium-catalyzed electrochemical phosphonation of C(sp2)–H bond. J Organomet Chem 785:68–71 Gryaznova TV, Dudkina YB, Islamov DR, Kataeva ON, Sinyashin OG, Vicic DA, Budnikova Y (2015) Pyridine-directed palladium-catalyzed electrochemical phosphonation of C(sp2)–H bond. J Organomet Chem 785:68–71
57.
Zurück zum Zitat Dudkina YB, Gryaznova TV, Kataeva ON, Budnikova YH, Sinyashin OG (2014) Electrochemical CH phosphorylation of 2-phenylpyridine in the presence of palladium salts. Russ Chem Bull 63:2641–2646 Dudkina YB, Gryaznova TV, Kataeva ON, Budnikova YH, Sinyashin OG (2014) Electrochemical CH phosphorylation of 2-phenylpyridine in the presence of palladium salts. Russ Chem Bull 63:2641–2646
58.
Zurück zum Zitat Khrizanforov MN, Strekalova SO, Gryaznova TV, Khrizanforova VV, Budnikova YH (2015) New method of metal-induced oxidative phosphorylation of benzene. Russ Chem Bull 64:1926–1932 Khrizanforov MN, Strekalova SO, Gryaznova TV, Khrizanforova VV, Budnikova YH (2015) New method of metal-induced oxidative phosphorylation of benzene. Russ Chem Bull 64:1926–1932
59.
Zurück zum Zitat Jutand A (2008) Contribution of electrochemistry to organometallic catalysis. Chem Rev 108:2300–2347PubMed Jutand A (2008) Contribution of electrochemistry to organometallic catalysis. Chem Rev 108:2300–2347PubMed
60.
Zurück zum Zitat Budnikova YH (2002) Metal complex catalysis in organic electrosynthesis. Russ Chem Rev 71:111–139 Budnikova YH (2002) Metal complex catalysis in organic electrosynthesis. Russ Chem Rev 71:111–139
61.
Zurück zum Zitat Budnikova YH, Yakhvarov DG, Kargin YM (1997) Arylation and alkylation of white phosphorus in the presence of electrochemically generated nickel (0) complexes. Mendeleev Commun 7:67–68 Budnikova YH, Yakhvarov DG, Kargin YM (1997) Arylation and alkylation of white phosphorus in the presence of electrochemically generated nickel (0) complexes. Mendeleev Commun 7:67–68
62.
Zurück zum Zitat Budnikova YH, Kargin YM, Perichon J, Nedelec JY (1999) Nickel-catalysed electrochemical coupling between mono-or di-chlorophenylphosphines and aryl or heteroaryl halides. J Organomet Chem 575:63–66 Budnikova YH, Kargin YM, Perichon J, Nedelec JY (1999) Nickel-catalysed electrochemical coupling between mono-or di-chlorophenylphosphines and aryl or heteroaryl halides. J Organomet Chem 575:63–66
63.
Zurück zum Zitat Klein A, Budnikova YH, Sinyashin OG (2007) Electron transfer in organonickel complexes of α-diimines: versatile redox catalysts for C–C or C–P coupling reactions–a review. J Organomet Chem 692:3156–3166 Klein A, Budnikova YH, Sinyashin OG (2007) Electron transfer in organonickel complexes of α-diimines: versatile redox catalysts for C–C or C–P coupling reactions–a review. J Organomet Chem 692:3156–3166
64.
Zurück zum Zitat Frontana-Uribe BA, Little RD, Ibanez JG, Palma A, Vasquez-Medrano R (2010) Organic electrosynthesis: a promising green methodology in organic chemistry. Green Chem 12:2099–2119 Frontana-Uribe BA, Little RD, Ibanez JG, Palma A, Vasquez-Medrano R (2010) Organic electrosynthesis: a promising green methodology in organic chemistry. Green Chem 12:2099–2119
65.
Zurück zum Zitat Yoshida J, Kataoka K, Horcajada R, Nagaki A (2008) Modern strategies in electroorganic synthesis. Chem Rev 108:2265–2299PubMed Yoshida J, Kataoka K, Horcajada R, Nagaki A (2008) Modern strategies in electroorganic synthesis. Chem Rev 108:2265–2299PubMed
66.
Zurück zum Zitat Fuchigami T, Atobe M, Inagi S (2014) Fundamentals and applications of organic electrochemistry: synthesis, materials, devices. Wiley, Chichester Fuchigami T, Atobe M, Inagi S (2014) Fundamentals and applications of organic electrochemistry: synthesis, materials, devices. Wiley, Chichester
67.
Zurück zum Zitat Milyukov VA, Budnikova YH, Sinyashin OG (2005) Organic chemistry of elemental phosphorus. Russ Chem Rev 74:781–805 Milyukov VA, Budnikova YH, Sinyashin OG (2005) Organic chemistry of elemental phosphorus. Russ Chem Rev 74:781–805
68.
Zurück zum Zitat Dudkina YB, Khrizanforov MN, Gryaznova TV, Budnikova YH (2014) Prospects of synthetic electrochemistry in the development of new methods of electrocatalytic fluoroalkylation. J Organomet Chem 751:301–305 Dudkina YB, Khrizanforov MN, Gryaznova TV, Budnikova YH (2014) Prospects of synthetic electrochemistry in the development of new methods of electrocatalytic fluoroalkylation. J Organomet Chem 751:301–305
69.
Zurück zum Zitat Dudkina YB, Mikhaylov DY, Gryaznova TV, Tufatullin AI, Kataeva ON, Vicic DA, Budnikova YH (2013) Electrochemical ortho functionalization of 2-phenylpyridine with perfluorocarboxylic acids catalyzed by palladium in higher oxidation states. Organometallics 32:4785–4792 Dudkina YB, Mikhaylov DY, Gryaznova TV, Tufatullin AI, Kataeva ON, Vicic DA, Budnikova YH (2013) Electrochemical ortho functionalization of 2-phenylpyridine with perfluorocarboxylic acids catalyzed by palladium in higher oxidation states. Organometallics 32:4785–4792
70.
Zurück zum Zitat Dudkina YB, Mikhaylov DY, Gryaznova TV, Sinyashin OG, Vicic DA, Budnikova YH (2012) MII/MIII-catalyzed ortho-fluoroalkylation of 2-phenylpyridine. Eur J Org Chem 2012:2114–2117 Dudkina YB, Mikhaylov DY, Gryaznova TV, Sinyashin OG, Vicic DA, Budnikova YH (2012) MII/MIII-catalyzed ortho-fluoroalkylation of 2-phenylpyridine. Eur J Org Chem 2012:2114–2117
71.
Zurück zum Zitat Khrizanforov M, Gryaznova T, Sinyashin O, Budnikova Y (2012) Aromatic perfluoroalkylation with metal complexes in electrocatalytic conditions. J Organomet Chem 718:101–104 Khrizanforov M, Gryaznova T, Sinyashin O, Budnikova Y (2012) Aromatic perfluoroalkylation with metal complexes in electrocatalytic conditions. J Organomet Chem 718:101–104
72.
Zurück zum Zitat Dudkina YB, Gryaznova TV, Osin YN, Salnikov VV, Davydov NA, Fedorenko SV, Mustafina AR, Vicic DA, Sinyashin OG, Budnikova YH (2015) Nanoheterogeneous catalysis in electrochemically induced olefin perfluoroalkylation. Dalton Trans 44:8833–8838PubMed Dudkina YB, Gryaznova TV, Osin YN, Salnikov VV, Davydov NA, Fedorenko SV, Mustafina AR, Vicic DA, Sinyashin OG, Budnikova YH (2015) Nanoheterogeneous catalysis in electrochemically induced olefin perfluoroalkylation. Dalton Trans 44:8833–8838PubMed
73.
Zurück zum Zitat Khrizanforov M, Strekalova S, Khrizanforova V, Grinenko V, Kholin K, Kadirov M, Burganov T, Gubaidullin A, Gryaznova T, Sinyashin O, Xu L, Vicic DA, Budnikova Y (2015) Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes. Dalton Trans 44:19674–19681PubMed Khrizanforov M, Strekalova S, Khrizanforova V, Grinenko V, Kholin K, Kadirov M, Burganov T, Gubaidullin A, Gryaznova T, Sinyashin O, Xu L, Vicic DA, Budnikova Y (2015) Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes. Dalton Trans 44:19674–19681PubMed
74.
Zurück zum Zitat Mikhaylov D, Gryaznova T, Dudkina Y, Khrizanphorov M, Latypov S, Kataeva O, Vicic DA, Sinyashin OG, Budnikova Y (2012) Electrochemical nickel-induced fluoroalkylation: synthetic, structural and mechanistic study. Dalton Trans 41:165–172PubMed Mikhaylov D, Gryaznova T, Dudkina Y, Khrizanphorov M, Latypov S, Kataeva O, Vicic DA, Sinyashin OG, Budnikova Y (2012) Electrochemical nickel-induced fluoroalkylation: synthetic, structural and mechanistic study. Dalton Trans 41:165–172PubMed
75.
Zurück zum Zitat Khrizanforov MN, Fedorenko SV, Strekalova SO, Kholin KV, Mustafina AR, Zhilkin MY, Khrizanforova VV, Osin YN, Salnikov VV, Gryaznova TV, Budnikova YH (2016) Ni (iii) complex stabilized by silica nanoparticles as an efficient nanoheterogeneous catalyst for oxidative C–H fluoroalkylation. Dalton Trans 45:11976–11982PubMed Khrizanforov MN, Fedorenko SV, Strekalova SO, Kholin KV, Mustafina AR, Zhilkin MY, Khrizanforova VV, Osin YN, Salnikov VV, Gryaznova TV, Budnikova YH (2016) Ni (iii) complex stabilized by silica nanoparticles as an efficient nanoheterogeneous catalyst for oxidative C–H fluoroalkylation. Dalton Trans 45:11976–11982PubMed
76.
Zurück zum Zitat Dudkina YB, Kholin KV, Gryaznova TV, Islamov DR, Kataeva ON, Rizvanov IK, Levitskaya AI, Fominykh OD, Balakina MY, Sinyashin OG, Budnikova YH (2017) Redox trends in cyclometalated palladium (II) complexes. Dalton Trans 46:165–177 Dudkina YB, Kholin KV, Gryaznova TV, Islamov DR, Kataeva ON, Rizvanov IK, Levitskaya AI, Fominykh OD, Balakina MY, Sinyashin OG, Budnikova YH (2017) Redox trends in cyclometalated palladium (II) complexes. Dalton Trans 46:165–177
77.
Zurück zum Zitat Mikhaylov DY, Budnikova YH, Gryaznova TV, Krivolapov DV, Litvinov IA, Vicic DA, Sinyashin OG (2009) Electrocatalytic fluoroalkylation of olefins. J Organomet Chem 694:3840–3843 Mikhaylov DY, Budnikova YH, Gryaznova TV, Krivolapov DV, Litvinov IA, Vicic DA, Sinyashin OG (2009) Electrocatalytic fluoroalkylation of olefins. J Organomet Chem 694:3840–3843
78.
Zurück zum Zitat Wei D, Zhu X, Niu JL, Song MP (2016) High-valent-cobalt-catalyzed C–H functionalization based on concerted metalation–deprotonation and single-electron-transfer mechanisms. ChemCatChem 8:1242–1263 Wei D, Zhu X, Niu JL, Song MP (2016) High-valent-cobalt-catalyzed C–H functionalization based on concerted metalation–deprotonation and single-electron-transfer mechanisms. ChemCatChem 8:1242–1263
79.
Zurück zum Zitat Pellissier H, Clavier H (2014) Enantioselective cobalt-catalyzed transformations. Chem Rev 114:2775–2823PubMed Pellissier H, Clavier H (2014) Enantioselective cobalt-catalyzed transformations. Chem Rev 114:2775–2823PubMed
80.
Zurück zum Zitat Tilly D, Dayaker G, Bachu P (2014) Cobalt mediated C–H bond functionalization: emerging tools for organic synthesis. Catal Sci Technol 4:2756–2777 Tilly D, Dayaker G, Bachu P (2014) Cobalt mediated C–H bond functionalization: emerging tools for organic synthesis. Catal Sci Technol 4:2756–2777
81.
Zurück zum Zitat Cahiez G, Moyeux A (2010) Cobalt-catalyzed cross-coupling reactions. Chem Rev 110:1435–1462PubMed Cahiez G, Moyeux A (2010) Cobalt-catalyzed cross-coupling reactions. Chem Rev 110:1435–1462PubMed
82.
Zurück zum Zitat Hess W, Treutwein J, Hilt G (2008) Cobalt-catalysed carbon-carbon bond-formation reactions. Synthesis 22:3537–3562 Hess W, Treutwein J, Hilt G (2008) Cobalt-catalysed carbon-carbon bond-formation reactions. Synthesis 22:3537–3562
83.
Zurück zum Zitat Byrne FP, Jin S, Paggiola G, Petchey THM, Clark JH, Farmer TJ, Hunt AJ, McElroy CR, Sherwood J (2016) Tools and techniques for solvent selection: green solvent selection guides. Sustain Chem Process 4:1–7 Byrne FP, Jin S, Paggiola G, Petchey THM, Clark JH, Farmer TJ, Hunt AJ, McElroy CR, Sherwood J (2016) Tools and techniques for solvent selection: green solvent selection guides. Sustain Chem Process 4:1–7
84.
Zurück zum Zitat Arends I, Sheldon R, Hanefeld U (2007) Green chemistry and catalysis. Wiley, Weinheim Arends I, Sheldon R, Hanefeld U (2007) Green chemistry and catalysis. Wiley, Weinheim
85.
Zurück zum Zitat Kemeling GM (2012) Solvent choices and sustainable chemistry. ChemSusChem 5:2291–2292PubMed Kemeling GM (2012) Solvent choices and sustainable chemistry. ChemSusChem 5:2291–2292PubMed
86.
Zurück zum Zitat Izutsu K (2009) Electrochemistry in nonaqueous solutions, 2nd edn. Wiley, Weinheim Izutsu K (2009) Electrochemistry in nonaqueous solutions, 2nd edn. Wiley, Weinheim
87.
Zurück zum Zitat Luca OR, Gustafson JL, Maddox SM, Fenwicka AQ, Smith DC (2015) Catalysis by electrons and holes: formal potential scales and preparative organic electrochemistry. Org Chem Front 2:823–848 Luca OR, Gustafson JL, Maddox SM, Fenwicka AQ, Smith DC (2015) Catalysis by electrons and holes: formal potential scales and preparative organic electrochemistry. Org Chem Front 2:823–848
88.
Zurück zum Zitat Polleux L, Labbé E, Buriez O, Périchon J (2005) CoI- and Co0-bipyridine complexes obtained by reduction of CoBr2bpy: electrochemical behaviour and investigation of their reactions with aromatic halides and vinylic acetates. Chem Eur J 11:4678–4686PubMed Polleux L, Labbé E, Buriez O, Périchon J (2005) CoI- and Co0-bipyridine complexes obtained by reduction of CoBr2bpy: electrochemical behaviour and investigation of their reactions with aromatic halides and vinylic acetates. Chem Eur J 11:4678–4686PubMed
89.
Zurück zum Zitat Gomes P, Gosmini C, Nédélec J-Y, Périchon J (2000) Cobalt bromide as catalyst in electrochemical addition of aryl halides onto activated olefins. Tetrahedron Lett 41:3385–3388 Gomes P, Gosmini C, Nédélec J-Y, Périchon J (2000) Cobalt bromide as catalyst in electrochemical addition of aryl halides onto activated olefins. Tetrahedron Lett 41:3385–3388
90.
Zurück zum Zitat Budnikova YG, Kafiyatullina AG, Kargin YM, Sinyashin OG (2003) Electrochemical reduction of cobalt and nickel complexes with ligands stabilizing metal in low oxidation state. Russ Chem Bull 52:1504–1511 Budnikova YG, Kafiyatullina AG, Kargin YM, Sinyashin OG (2003) Electrochemical reduction of cobalt and nickel complexes with ligands stabilizing metal in low oxidation state. Russ Chem Bull 52:1504–1511
91.
Zurück zum Zitat Budnikova YG, Kafiyatullina AG, Kargin YM, Sinyashin OG (2001) Kinetic regularities of electrochemical reduction of organic halides under the action of cobalt complexes with 2,2′-bipyridine. Russ J Gen Chem 71:231–233 Budnikova YG, Kafiyatullina AG, Kargin YM, Sinyashin OG (2001) Kinetic regularities of electrochemical reduction of organic halides under the action of cobalt complexes with 2,2′-bipyridine. Russ J Gen Chem 71:231–233
92.
Zurück zum Zitat Buettner GR (1987) Spin trapping: ESR parameters of spin adducts 1474 1528V. Free Radical Biol Med 3:259–303 Buettner GR (1987) Spin trapping: ESR parameters of spin adducts 1474 1528V. Free Radical Biol Med 3:259–303
93.
Zurück zum Zitat Haire LD, Krygsman PH, Janzen EG, Oehler UM (1988) Correlation of radical structure with EPR spin adduct parameters: utility of the proton, carbon-13, and nitrogen-14 hyperfine splitting constants of aminoxyl adducts of PBN-nitronyl-13C for three-parameter scatter plots. J Org Chem 53:4535–4542 Haire LD, Krygsman PH, Janzen EG, Oehler UM (1988) Correlation of radical structure with EPR spin adduct parameters: utility of the proton, carbon-13, and nitrogen-14 hyperfine splitting constants of aminoxyl adducts of PBN-nitronyl-13C for three-parameter scatter plots. J Org Chem 53:4535–4542
94.
Zurück zum Zitat Sheberla D, Tumanskii B, Tomasik AC, Mitra A, Hill NJ, West R, Apeloig Y (2010) Different electronic structure of phosphonyl radical adducts of N-heterocyclic carbenes, silylenes and germylenes: EPR spectroscopic study and DFT calculations. Chem Sci 1:234–241 Sheberla D, Tumanskii B, Tomasik AC, Mitra A, Hill NJ, West R, Apeloig Y (2010) Different electronic structure of phosphonyl radical adducts of N-heterocyclic carbenes, silylenes and germylenes: EPR spectroscopic study and DFT calculations. Chem Sci 1:234–241
95.
Zurück zum Zitat Tumanskii B, Sheberla D, Molev G, Apeloig Y (2007) Dual character of arduengo carbene–radical adducts: addition versus coordination product. Angew Chem Int Ed 46:7408–7411 Tumanskii B, Sheberla D, Molev G, Apeloig Y (2007) Dual character of arduengo carbene–radical adducts: addition versus coordination product. Angew Chem Int Ed 46:7408–7411
96.
Zurück zum Zitat Hoffman R (2007) Phosphorus-31 NMR. Hebrew University, Jerusalem Hoffman R (2007) Phosphorus-31 NMR. Hebrew University, Jerusalem
97.
Zurück zum Zitat Tang S, Liu Y, Lei A (2018) Electrochemical oxidative cross-coupling with hydrogen evolution: a green and sustainable way for bond formation cell. Chem 4(1):27–45 Tang S, Liu Y, Lei A (2018) Electrochemical oxidative cross-coupling with hydrogen evolution: a green and sustainable way for bond formation cell. Chem 4(1):27–45
Metadaten
Titel
Cobalt-Catalyzed Green Cross-Dehydrogenative C(sp2)-H/P-H Coupling Reactions
verfasst von
Mikhail Khrizanforov
Sofia Strekalova
Vera Khrizanforova
Alexey Dobrynin
Kirill Kholin
Tatyana Gryaznova
Valeriya Grinenko
Aidar Gubaidullin
M. K. Kadirov
Yulia Budnikova
Publikationsdatum
06.07.2018
Verlag
Springer US
Erschienen in
Topics in Catalysis / Ausgabe 18-19/2018
Print ISSN: 1022-5528
Elektronische ISSN: 1572-9028
DOI
https://doi.org/10.1007/s11244-018-1014-2

Weitere Artikel der Ausgabe 18-19/2018

Topics in Catalysis 18-19/2018 Zur Ausgabe

    Marktübersichten

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