Metal-free Catalytic Olefin Hydrogenation: Low-Temperature H2 Activation by Frustrated Lewis Pairs

被引：208

作者：

Greb, Lutz ^{[2
,4
]}

Ona-Burgos, Pascual ^{[2
]}

Schirmer, Birgitta ^{[3
]}

Grimme, Stefan ^{[1
]}

Stephan, Douglas W. ^{[4
]}

Paradies, Jan ^{[2
]}

机构：

[1] Univ Bonn, Mulliken Ctr Theoret Chem, Inst Phys & Theoret Chem, D-53115 Bonn, Germany

[2] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

[3] Univ Munster, Inst Organ Chem, D-4400 Munster, Germany

[4] Univ Toronto, Dept Chem, Toronto, ON M5S 1A1, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 40期

基金：

加拿大自然科学与工程研究理事会;

关键词：

alkenes; frustrated Lewis pairs; hydrogenation; olefin; phosphanes; HETEROLYTIC DIHYDROGEN ACTIVATION; H-2; ACTIVATION; NUCLEOPHILICITY; REDUCTION; IMINES; SCALES; SILYL; HYDROSILYLATION; REACTIVITY; CHEMISTRY;

D O I：

10.1002/anie.201204007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Weak nucleophiles for strong activation: The reversible activation of dihydrogen by an electron-deficient phosphine, (C 6F 5)PPh 2, in combination with the Lewis acid B(C 6F 5) 3 at -80 °C was accomplished. The catalytic hydrogenation of olefins proceeds through protonation and subsequent hydride attack. Electron-deficient phosphines and diarlyamines were demonstrated to be viable Lewis bases for the reaction, thus allowing catalyst loadings of 10 to 5 mol %. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10164 / 10168

页数：5

共 81 条

[41]

Noyori R, 2002, ANGEW CHEM INT EDIT, V41, P2008, DOI 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO

[42]

2-4

[43]

Noyori R., 2002, ANGEW CHEM, V114, P2108, DOI DOI 10.1016/J.MOLCATA.2004.03.014

[44] Enantioselective organocatalytic hydride reduction [J].

Ouellet, SG ;

Tuttle, JB ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :32-33

[45] Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters [J].

Ouellet, Stephane G. ;

Walji, Abbas M. ;

Macmillan, David W. C. .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1327-1339

[46]

Paradies J., 2011, ORG BIOMOL CHEM, V9, P4323

[47]

Phan T. B., 2006, ANGEW CHEM, V118, P3954

[48] Towards a general scale of nucleophilicity? [J].

Phan, Thanh Binh ;

Breugst, Martin ;

Mayr, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3869-3874

[49] Mechanistic Aspects of Bond Activation with Perfluoroarylboranes [J].

Piers, Warren E. ;

Marwitz, Adam J. V. ;

Mercier, Lauren G. .

INORGANIC CHEMISTRY, 2011, 50 (24) :12252-12262

[50] Pentafluorophenylboranes: from obscurity to applications [J].

Piers, WE ;

Chivers, T .

CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) :345-354

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