Cobalt Precursors for High-Throughput Discovery of Base Metal Asymmetric Alkene Hydrogenation Catalysts

被引:299
作者
Friedfeld, Max R. [1 ]
Shevlin, Michael [2 ]
Hoyt, Jordan M. [1 ]
Krska, Shane W. [2 ]
Tudge, Matthew T. [2 ]
Chirik, Paul J. [1 ]
机构
[1] Princeton Univ, Dept Chem, Princeton, NJ 08540 USA
[2] Merck Res Labs, Dept Proc Chem, Rahway, NJ 07065 USA
基金
美国国家科学基金会;
关键词
AMINO-ACID DERIVATIVES; COMPLEXES; REDUCTION; LIGANDS; MECHANISM; C=O;
D O I
10.1126/science.1243550
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Asymmetric hydrogenation of alkenes is one of the most widely used methods for the preparation of single enantiomer compounds, especially in the pharmaceutical and agrochemical industries. For more than four decades, precious metal complexes containing rhodium, iridium, and ruthenium have been predominantly used as catalysts. Here, we report rapid evaluation of libraries of chiral phosphine ligands with a set of simple cobalt precursors. From these studies, base metal precatalysts have been discovered for the hydrogenation of functionalized and unfunctionalized olefins with high enantiomeric excesses, demonstrating the potential utility of more earth-abundant metals in asymmetric hydrogenation.
引用
收藏
页码:1076 / 1080
页数:5
相关论文
共 38 条
[1]   KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2] [J].
ASHBY, MT ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :589-594
[2]   Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins [J].
Bell, S ;
Wüstenberg, B ;
Kaiser, S ;
Menges, F ;
Netscher, T ;
Pfaltz, A .
SCIENCE, 2006, 311 (5761) :642-644
[3]  
Blaser H U., 2010, Asymmetric Catalysis on Industrial Scale : Challenges , Approaches , and Solutions , 2nd ed
[4]   From a chiral switch to a ligand portfolio for asymmetric catalysis [J].
Blaser, Hans-Ulrich ;
Pugin, Benoit ;
Spindler, Felix ;
Thommen, Marc .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1240-1250
[5]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[6]   The Growing Impact of Catalysis in the Pharmaceutical Industry [J].
Busacca, Carl A. ;
Fandrick, Daniel R. ;
Song, Jinhua J. ;
Senanayake, Chris H. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1825-1864
[7]   Iridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents [J].
Church, Tamara L. ;
Andersson, Pher G. .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :513-531
[8]   OPTICALLY-ACTIVE COMPLEXES OF TRANSITION-METALS (RH(I), RU(II), CO(II) AND NI(II)) WITH 2-AMINOCARBONYLPYRROLIDINE LIGANDS - SELECTIVE CATALYSTS FOR HYDROGENATION OF PROCHIRAL OLEFINS [J].
CORMA, A ;
IGLESIAS, M ;
DELPINO, C ;
SANCHEZ, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 431 (02) :233-246
[9]  
Cozzi PG, 2001, ADV SYNTH CATAL, V343, P450, DOI 10.1002/1615-4169(200107)343:5<450::AID-ADSC450>3.0.CO
[10]  
2-7