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

被引：335

作者：

Chase, Preston A. ^{[1
]}

Stephan, Douglas W. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 39期

基金：

加拿大自然科学与工程研究理事会;

关键词：

boranes; carbenes; donor-acceptor systems; hydrogen; steric hindrance;

D O I：

10.1002/anie.200802596

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Size matters: The frustrated Lewis pair derived from B(C6F5)3 and the sterically encumbered N-heterocyclic carbene N,N′-tBu2C3H 2N2 (1) cleaves dihydrogen heterolytically to give a imidazolium borate (see scheme, left), and cleaves amine N-H bonds to form aminoborate salts (right) or aminoboranes. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7433 / 7437

页数：5

共 45 条

[1] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[2]

Bettinger H. F., 2008, ANGEW CHEM, V120, P4822

[3] Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene [J].

Bettinger, Holger F. ;

Filthaus, Matthias ;

Bornemann, Holger ;

Oppel, Iris M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4744-4747

[4] Pericyclic reactions between aminoboranes R2B=NR2′ and alkenes:: [4+2] vs [2+2] transition states [J].

Bissett, KA ;

Gilbert, TA .

ORGANOMETALLICS, 2004, 23 (04) :850-854

[5] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

CHEMICAL REVIEWS, 2000, 100 (01) :39-91

[6] Pyridine and phosphine reactions with [CPh3][B(C6F5)4] [J].

Cabrera, Lourdes ;

Welch, Gregory C. ;

Masuda, Jason D. ;

Wei, Pingrong ;

Stephan, Douglas W. .

INORGANICA CHIMICA ACTA, 2006, 359 (09) :3066-3071

[7] Metal-free catalytic hydrogenation (vol 46, pg 8050, 2007) [J].

Chase, P. A. ;

Welch, G. C. ;

Jurca, T. ;

Stephan, D. W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9136-9136

[8]

Chase P. A., 2007, Angew. Chem., V119

[9]

CHASE PA, 2007, ANGEW CHEM, V119, P9296

[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

← 1 2 3 4 5 →