Skip to main content
Fachgebiete
Automobil + Motoren Bauwesen + Immobilien Business IT + Informatik Elektrotechnik + Elektronik Energie + Nachhaltigkeit Finance + Banking Management + Führung Marketing + Vertrieb Maschinenbau + Werkstoffe Versicherung + Risiko
DE
EN
Themenseiten
Organisationspsychologie Projektmanagement Marketing Smart Manufacturing
Bücher
Zeitschriften
Weitere Formate
Podcasts Webinare Technik Webinare Wirtschaft Kongresse Veranstaltungskalender Awards
Jetzt Einzelzugang starten
Zugang für Unternehmen
Referenzkunden
MTZ-Fachkongress

Antriebe und Energiesysteme von morgen


Austausch von Automobil- und Energiewirtschaft

Am 14./15. Mai geht es in Chemnitz um die Mobilitätswende durch Elektro- und Wasserstofffahrzeuge.
Erweiterte Suche
Anmelden
nach oben
Erschienen in:
Discovery of Frustrated Lewis Pairs: Intermolecular FLPs for Activation of Small Molecules Kapitel lesen Erstes Kapitel lesen

2013 | OriginalPaper | Buchkapitel

Frustrated Lewis Pair Mediated Hydrogenations

verfasst von : Douglas W. Stephan, Gerhard Erker

Erschienen in: Frustrated Lewis Pairs I

Verlag: Springer Berlin Heidelberg

Einloggen

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

search-config
loading …

Abstract

The development and use of frustrated Lewis pairs (FLPs) as both stoichiometric and catalytic reductants for the hydrogenation of a variety of organic substrate is described.

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!

Jetzt informieren

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!

Jetzt informieren

Springer Professional "Wirtschaft"

Online-Abonnement

Mit Springer Professional "Wirtschaft" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 340 Zeitschriften

aus folgenden Fachgebieten:

  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Versicherung + Risiko




Jetzt Wissensvorsprung sichern!

Jetzt informieren
Vorheriges Kapitel Intramolecular Frustrated Lewis Pairs: Formation and Chemical Features
Nächstes Kapitel Amine-Borane Mediated Metal-Free Hydrogen Activation and Catalytic Hydrogenation
Fußnoten
1
No reaction was observed when 3a was reacted with 1 or 2 and 1/2 in the absence of hydrogen.
 
Literatur
1.
Mozingo R (1946) Palladium catalysts. Org Synth 26:77
2.
Osborn JA, Jardine FH, Young JF, Wilkinso G (1966) Preparation and properties of tris(triphenylphosphine)halogenorhodium(1) and some reactions thereof including catalytic homogeneous hydrogenation of olefins and acetylenes and their derivatives. J Chem Soc A 1711
3.
Noyori R (2002) Asymmetric catalysis: science and opportunities (Nobel Lecture). Angew Chem Int Ed 41:2008CrossRef
4.
5.
Dewitt EJ, Trapasso LE, Ramp FL (1961) Homogeneous hydrogenation catalyzed by boranes. J Am Chem Soc 83:4672CrossRef
6.
Ramp FL, Dewitt EJ, Trapasso LE (1962) Homogeneous hydrogenation catalyzed by boranes. J Org Chem 27:4368CrossRef
7.
Siskin M (1974) Strong acid chemistry. 2. Catalytic-hydrogenation of aromatics in hydrogen fluoride-tantalum pentafluoride and related strong acid systems. J Am Chem Soc 96:3641CrossRef
8.
Wristers J (1975) Strong acid-catalyzed hydrogenation of aromatics. J Am Chem Soc 97:4312CrossRef
9.
Yalpani M, Lunow T, Köster R (1989) Reduction of polycyclic arenes by BH-boranes. 2. Borane catalyzed hydrogenation of naphthalenes to tetralins. Chem Ber 122:687CrossRef
10.
Yalpani M, Köster R (1990) Partial hydrogenation – from anthracene to coronene. Chem Ber 123:719CrossRef
11.
Yalpani M, Koster R, Haenel MW (1990) Reductions of polycyclic arenes by B–H boranes. 4. Coal-tar hydrogenation catalyzed by B–H boranes. Erdol Kohle Erdgas P 43:344
12.
Kötting C, Sander W (1999) Insertion of difluorovinylidene into hydrogen and methane. J Am Chem Soc 121:8891CrossRef
13.
Sander W, Kötting C (1999) Reactions of difluorovinylidene – a super-electrophilic carbene. Chem Eur J 5:24CrossRef
14.
Sander W, Hubert R, Kraka E, Grafenstein J, Cremer D (2000) 4-Oxo-2,3,5,6-tetrafluorocyclohexa-2,5-dienylidene – a highly electrophilic triplet carbene. Chem Eur J 6:4567CrossRef
15.
Haenel MW, Narangerel J, Richter UB, Rufinska A (2006) The first liquefaction of high-rank bituminous coals by preceding hydrogenation with homogeneous borane or iodine catalysts. Angew Chem Int Ed 45:1061. doi:10.​1002/​anie.​200502614 CrossRef
16.
Frey GD, Lavallo V, Donnadieu B, Schoeller WW, Bertrand G (2007) Carbenes reacting like metals, oxidative addition of H2 and NH3. Science 316:439CrossRef
17.
Bettinger HF, Filthaus M, Neuhaus P (2009) Insertion into dihydrogen employing the nitrogen centre of a borylnitrene. Chem Commun 2186. doi:10.1039/B817270f
18.
Bettinger HF, Filthaus M, Bornemann H, Oppel IM (2008) Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene. Angew Chem Int Ed 47:4744. doi:10.​1002/​anie.​200705936 CrossRef
19.
20.
Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G (2008) Metal-free catalytic hydrogenation of enamines, imines, and conjugated phosphinoalkenylboranes. Angew Chem Int Ed 47:7543. doi:10.​1002/​anie.​200801432 CrossRef
21.
Schwendemann S, Tumay TA, Axenov KV, Peuser I, Kehr G, Fröhlich R, Erker G (2010) Metal-free frustrated Lewis pair catalyzed 1,4-hydrogenation of conjugated metallocene dienamines. Organometallics 29:1067. doi:10.​1021/​Om900963p CrossRef
22.
Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown CC, Heiden ZM, Welch GC, Ullrich M (2011) Metal-free catalytic hydrogenation of polar substrates by frustrated Lewis pairs. Inorg Chem 50:12338CrossRef
23.
Welch GC, Prieto R, Dureen MA, Lough AJ, Labeodan OA, Holtrichter-Rossmann T, Stephan DW (2009) Reactions of phosphines with electron deficient boranes. Dalton Trans 1559. doi:10.1039/B814486a
24.
Chase PA, Jurca T, Stephan DW (2008) Lewis acid-catalyzed hydrogenation: B(C6F5)3-mediated reduction of imines and nitriles with H2. Chem Commun 1701. doi:10.1039/B718598g
25.
Chen DJ, Klankermayer J (2008) Metal-free catalytic hydrogenation of imines with tris(perfluorophenyl) borane. Chem Commun 2130. doi:10.1039/B801806e
26.
27.
Rokob TA, Hamza A, Papai I (2009) Rationalizing the reactivity of frustrated Lewis pairs: thermodynamics of H2 activation and the role of acid–base properties. J Am Chem Soc 131:10701. doi:10.​1021/​Ja903878z CrossRef
28.
Eros G, Mehdi H, Papai I, Rokob TA, Kiraly P, Tarkanyi G, Soos T (2010) Expanding the scope of metal-free catalytic hydrogenation through frustrated Lewis pair design. Angew Chem Int Ed 49:6559. doi:10.​1002/​anie.​201001518 CrossRef
29.
Rokob TA, Hamza A, Stirling A, Papai I (2009) On the mechanism of B(C6F5)3-catalyzed direct hydrogenation of imines: inherent and thermally induced frustration. J Am Chem Soc 131:2029. doi:10.​1021/​Ja809125r CrossRef
30.
Rokob TA, Hamza A, Stirling A, Soos T, Papai I (2008) Turning frustration into bond activation: a theoretical mechanistic study on heterolytic hydrogen splitting by frustrated Lewis pairs. Angew Chem Int Ed 47:2435. doi:10.​1002/​anie.​200705586 CrossRef
31.
Stirling A, Hamza A, Rokob TA, Papai I (2008) Concerted attack of frustrated Lewis acid–base pairs on olefinic double bonds: a theoretical study. Chem Commun 3148. doi:10.1039/B804662j
32.
Spies P, Erker G, Kehr G, Bergander K, Fröhlich R, Grimme S, Stephan DW (2007) Rapid intramolecular heterolytic dihydrogen activation by a four-membered heterocyclic phosphane–borane adduct. Chem Commun 5072. doi:10.1039/B710475h
33.
34.
Mömming CM, Fromel S, Kehr G, Fröhlich R, Grimme S, Erker G (2009) Reactions of an intramolecular frustrated Lewis pair with unsaturated substrates: evidence for a concerted olefin addition reaction. J Am Chem Soc 131:12280. doi:10.​1021/​Ja903511s CrossRef
35.
Thomson JW, Hatnean JA, Hastie JJ, Pasternak A, Stephan DW, Chase PA (2012) Scrubbers for metal-free hydrogenation catalysts (submitted)
36.
Axenov KV, Kehr G, Frohlich R, Erker G (2009) Functional group chemistry at the Group 4 bent metallocene frameworks: formation and "metal-free" catalytic hydrogenation of bis(imino-Cp)zirconium complexes. Organometallics 28:5148. doi:10.​1021/​Om9004093 CrossRef
37.
Axenov KV, Kehr G, Fröhlich R, Erker G (2009) Catalytic hydrogenation of sensitive organometallic compounds by antagonistic N/B Lewis pair catalyst systems. J Am Chem Soc 131:3454. doi:10.​1021/​Ja8100006 CrossRef
38.
Jiang CF, Blacque O, Berke H (2009) Metal-free hydrogen activation and hydrogenation of imines by 1,8-bis(dipentafluorophenylboryl)naphthalene. Chem Commun 5518. doi:10.1039/B909620e
39.
Eros G, Nagy K, Mehdi H, Papai I, Nagy P, Kiraly P, Tarkanyi G, Soos T (2012) Catalytic hydrogenation with frustrated Lewis pairs: selectivity achieved by size-exclusion design of Lewis acids. Chem Eur J 18:574. doi:10.​1002/​chem.​201102438 CrossRef
40.
Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskela M, Repo T, Pyykko P, Rieger B (2008) Molecular tweezers for hydrogen: synthesis, characterization, and reactivity. J Am Chem Soc 130:14117. doi:10.​1021/​Ja806627s CrossRef
41.
42.
43.
Chen DJ, Schmitkamp M, Francio G, Klankermayer J, Leitner W (2008) Enantioselective hydrogenation with racemic and enantiopure binap in the presence of a chiral ionic liquid. Angew Chem Int Ed 47:7339. doi:10.​1002/​anie.​200801995 CrossRef
44.
Wang HD, Fröhlich R, Kehr G, Erker G (2008) Heterolytic dihydrogen activation with the 1,8-bis(diphenylphosphino)-naphthalene/B(C6F5)3 pair and its application for metal-free catalytic hydrogenation of silyl enol ethers. Chem Commun 5966. doi:10.1039/B813286k
45.
46.
47.
Spannhoff K (2010) C1-Verbrückte Diphosphine in Organometallchemie und frustrierten Lewis-Paaren, doctoral dissertation: Universität Münster
48.
Parks DJ, Spence REVH, Piers WE (1995) Bis(pentafluorophenyl)borane – synthesis, properties, and hydroboration chemistry of a highly electrophilic borane reagent. Angew Chem Int Ed Engl 34:809CrossRef
49.
Parks DJ, Piers WE, Yap GPA (1998) Synthesis, properties, and hydroboration activity of the highly electrophilic borane bis(pentafluorophenyl)borane, HB(C6F5)2. Organometallics 17:5492CrossRef
50.
Spence REV, Piers WE, Sun YM, Parvez M, MacGillivray LR, Zaworotko MJ (1998) Mechanistic aspects of the reactions of bis(pentafluorophenyl)borane with the dialkyl zirconocenes Cp2ZrR2 (R = CH3, CH2SiMe3, and CH2C6H5). Organometallics 17:2459CrossRef
51.
52.
Greb L, Ono-Burgos P, Schirmer B, Breher F, Grimme S, Stephan DW, Paradies J (2012) Metal-free catalytic olefin hydrogenations: low temperature H2-activation by frustrated Lewis pairs. Angew Chem Int Ed Engl 51:10164–10168CrossRef
53.
54.
Xu BH, Kehr G, Frohlich R, Wibbeling B, Schirmer B, Grimme S, Erker G (2011) Reaction of frustrated Lewis pairs with conjugated ynones-selective hydrogenation of the carbon–carbon triple bond. Angew Chem Int Ed 50:7183. doi:10.​1002/​anie.​201101051 CrossRef
55.
Chen C, Eweiner F, Wibbeling B, Fröhlich R, Senda S, Ohki Y, Tatsumi K, Grimme S, Kehr G, Erker G (2010) Exploring the limits of frustrated Lewis pair chemistry with alkynes: detection of a system that favors 1,1-carboboration over cooperative 1,2-P/B-addition. Chem Asian J 5:2199. doi:10.​1002/​asia.​201000189 CrossRef
56.
57.
Chen C, Voss T, Frohlich R, Kehr G, Erker G (2011) 1,1-Carboboration of 1-alkynes: a conceptual alternative to the hydroboration reaction. Org Lett 13:62. doi:10.​1021/​Ol102544x CrossRef
58.
59.
Wrackmeyer B (1995) 1,1-Organoboration of alkynylsilicon, -germanium, -tin and -lead compounds. Coord Chem Rev 145:125
60.
61.
Reddy JS, Xu B, Mahdi T, Kehr G, Fröhlich R, Stephan DW, Erker G (2012) Alkenylboranes derived frustrated Lewis pairs: metal-free catalytic hydrogenation reactions of electron-deficient alkenes. Organometallics. doi:10.​1021/​om3006068
62.
63.
Mahdi T, Heiden ZM, Grimme S, Stephan DW (2012) Metal-free aromatic hydrogenation: aniline to cyclohexyl-amine derivatives. J Am Chem Soc 134:4088. doi:10.​1021/​Ja300228a CrossRef
64.
Millot N, Santini CC, Fenet B, Basset JM (2002) Formation and characterization of zwitterionic stereoisomers from the reaction of B(C6F5)3 and NEt2Ph: (E)- and (Z)-[EtPhN=CHCH2B(C6F5)3]. Eur J Inorg Chem 3328
65.
Metadaten
Titel
Frustrated Lewis Pair Mediated Hydrogenations
verfasst von
Douglas W. Stephan
Gerhard Erker
Copyright-Jahr
2013
Verlag
Springer Berlin Heidelberg
Buch
Frustrated Lewis Pairs I

Print ISBN: 978-3-642-36696-3

Electronic ISBN: 978-3-642-36697-0

Copyright-Jahr: 2013

DOI
https://doi.org/10.1007/128_2012_392

Premium Partner

    Marktübersichten

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

    Zur Marktübersicht
    Bildnachweise