Metal-free catalytic hydrogenation

被引:527
作者
Chase, Preston A. [1 ]
Welch, Gregory C. [1 ]
Jurca, Titel [1 ]
Stephan, Douglas W. [1 ]
机构
[1] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
关键词
boron; dihydrogen; homogeneous catalysis; hydrogenation; phosphorus;
D O I
10.1002/anie.200702908
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Phosphonium borates of the form R 2PH-(C6F4)BH(C6F5) 2 are shown to be metalfree hydrogenation catalysts (see scheme) that effect reduction of sterically hindered imines and aziridines, as well as B(C6F5)3-protected unhindered imines and nitriles, at relatively low H2 pressures and temperatures. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8050 / 8053
页数:4
相关论文
共 29 条
[1]   Ruthenium dihydride RuH2(PPh3)2((R,R)-cyclohexyldiamine) and ruthenium monohydride RuHCl(PPh3)2((R,R)-cyclohexyldiamine):: Active catalyst and catalyst precursor for the hydrogenation of ketones and imines [J].
Abdur-Rashid, K ;
Lough, AJ ;
Morris, RH .
ORGANOMETALLICS, 2000, 19 (14) :2655-2657
[2]   Mechanistic investigation on the hydrogenation of imines by [p-(Me2CH)C6H4Me]RuH(NH2CHPhCHPhNSO2C6H4-p-CH3).: Experimental support for an ionic pathway [J].
Aberg, Jenny B. ;
Samec, Joseph S. M. ;
Baeckvall, Jan-E. .
CHEMICAL COMMUNICATIONS, 2006, (26) :2771-2773
[4]  
[Anonymous], 2007, HDB HOMOGENEOU
[5]   Hydrogenation without a transition-metal catalyst:: On the mechanism of the base-catalyzed hydrogenation of ketones [J].
Berkessel, A ;
Schubert, TJS ;
Müller, TN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) :8693-8698
[6]   Solution and solid-state characteristics of imine adducts with tris(pentafluorophenyl)borane [J].
Blackwell, JM ;
Piers, WE ;
Parvez, M ;
McDonald, R .
ORGANOMETALLICS, 2002, 21 (07) :1400-1407
[7]   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
[8]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[9]   Lewis acid-catalyzed dimerization of N-unprotected aziridines [J].
Caiazzo, A ;
Dalili, S ;
Yudin, AK .
SYNLETT, 2003, (14) :2198-2202
[10]  
Clarke M. L., 2007, Handbook of Homogeneous Hydrogenation, P413