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

[1]

[Anonymous], 2010, COSMOTHERM VERSION C

[2]

[Anonymous], 2008, ANGEW CHEM

[3]

[Anonymous], 2012, ANGEW CHEM

[4] Tandem Frustrated Lewis Pair/Tris(pentafluorophenyl)borane-Catalyzed Deoxygenative Hydrosilylation of Carbon Dioxide [J].

Berkefeld, Andreas ;

Piers, Warren E. ;

Parvez, Masood .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) :10660-10661

[5] B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates [J].

Blackwell, JM ;

Sonmor, ER ;

Scoccitti, T ;

Piers, WE .

ORGANIC LETTERS, 2000, 2 (24) :3921-3923

[6] Reactions of substituted pyridines with electrophilic boranes [J].

Caputo, Christopher B. ;

Geier, Stephen J. ;

Winkelhaus, Daniel ;

Mitzel, Norbert W. ;

Vukotic, V. Nicolas ;

Loeb, Stephen J. ;

Stephan, Douglas W. .

DALTON TRANSACTIONS, 2012, 41 (07) :2131-2139

[7]

Chase P.A., 2007, Angewandte Chemie, V119, P8196, DOI DOI 10.1002/ANGE.200702908

[8]

Chase P.A., 2008, ANGEW CHEM, V120, P7543, DOI DOI 10.1002/ANGE.200802596

[9] Hydrogen and amine activation by a frustrated Lewis pair of a bulky n-heterocyclic carbene and B(C6F5)3 [J].

Chase, Preston A. ;

Stephan, Douglas W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7433-7437

[10] Lewis acid-catalyzed hydrogenation:: B(C6F5)3-mediated reduction of imines and nitriles with H2 [J].

Chase, Preston A. ;

Jurca, Titel ;

Stephan, Douglas W. .

CHEMICAL COMMUNICATIONS, 2008, (14) :1701-1703

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