Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis Pairs

被引:236
作者
Mahdi, Tayseer [1 ]
Stephan, Douglas W. [1 ,2 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
[2] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia
基金
加拿大自然科学与工程研究理事会;
关键词
METAL-FREE HYDROGENATION; HETEROLYTIC DIHYDROGEN ACTIVATION; CATIONIC RHODIUM COMPLEXES; ASYMMETRIC TRANSFER HYDROGENATION; HOMOGENEOUS HYDROGENATION; SELECTIVE HYDROGENATION; REDUCTION; CO2; ALDEHYDES; CARBONYL;
D O I
10.1021/ja508829x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hydrogenation of alkyl and aryl ketones using H-2 is catalytically achieved in 18 examples using 5 mol % B(C6F5)(3) in an ethereal solvent. In these cases the borane and ether behave as a frustrated Lewis pair to activate H-2 and effect the reduction.
引用
收藏
页码:15809 / 15812
页数:4
相关论文
共 69 条
[61]   Phosphine catalyzed reduction of CO2 with boranes [J].
Wang, Tongen ;
Stephan, Douglas W. .
CHEMICAL COMMUNICATIONS, 2014, 50 (53) :7007-7010
[62]   Carbene-9-BBN Ring Expansions as a Route to Intramolecular Frustrated Lewis Pairs for CO2 Reduction [J].
Wang, Tongen ;
Stephan, Douglas W. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (11) :3036-3039
[63]   Metal-Free HB(C6F5)2-Catalyzed Hydrogenation of Unfunctionalized Olefins and Mechanism Study of Borane-Mediated σ-Bond Metathesis [J].
Wang, Yuwen ;
Chen, Weiqiang ;
Lu, Zhenpin ;
Li, Zhen Hua ;
Wang, Huadong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) :7496-7499
[64]   A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed by Chiral Frustrated Lewis Pairs [J].
Wei, Simin ;
Du, Haifeng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (35) :12261-12264
[65]   Facile heterolytic cleavage of dihydrogen by phosphines and boranes [J].
Welch, Gregory C. ;
Stephan, Douglas W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1880-+
[66]   Reversible, metal-free hydrogen activation [J].
Welch, Gregory C. ;
Juan, Ronan R. San ;
Masuda, Jason D. ;
Stephan, Douglas W. .
SCIENCE, 2006, 314 (5802) :1124-1126
[67]   Reaction of Frustrated Lewis Pairs with Ketones and Esters [J].
Xu, Bao-Hua ;
Yanez, Raul Alfonso Adler ;
Nakatsuka, Hiroshi ;
Kitamura, Masato ;
Froehlich, Roland ;
Kehr, Gerald ;
Erker, Gerhard .
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (06) :1347-1356
[68]   HYDRIDE INTERMEDIATES IN HOMOGENEOUS HYDROGENATION REACTIONS OF OLEFINS AND ACETYLENES USING RHODIUM CATALYSTS [J].
YOUNG, JF ;
OSBORN, JA ;
JARDINE, FH ;
WILKINSO.G .
CHEMICAL COMMUNICATIONS, 1965, (07) :131-&
[69]   Amine(imine)diphosphine Iron Catalysts for Asymmetric Transfer Hydrogenation of Ketones and Imines [J].
Zuo, Weiwei ;
Lough, Alan J. ;
Li, Young Feng ;
Morris, Robert H. .
SCIENCE, 2013, 342 (6162) :1080-1083