Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Cobalt Pincer Complex

被引:251
作者
Mukherjee, Arup [1 ]
Srimani, Dipankar [1 ]
Chakraborty, Subrata [1 ]
Ben-David, Yehoshoa [1 ]
Milstein, David [1 ]
机构
[1] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel
基金
以色列科学基金会; 欧洲研究理事会;
关键词
ENVIRONMENTALLY BENIGN; ELECTRONIC-STRUCTURE; REDUCTIVE AMINATION; SECONDARY ALCOHOLS; IRON CATALYSTS; KETONES; MILD; EFFICIENT; AMMONIA; LIGAND;
D O I
10.1021/jacs.5b04879
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic hydrogenation of nitriles to primary amines represents an atom-efficient and environmentally benign reduction methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts, With a single exception. Here We report the first homogeneous Co-catalyzed hydrogenation of nitriles to primary amines. Several (hetero)aromatic, benzylic, and aliphatic nitriles undergo hydrogenation to the corresponding primary amines in good to excellent yields under the reaction conditions.
引用
收藏
页码:8888 / 8891
页数:4
相关论文
共 61 条
[1]   Amines made easily: A highly selective hydroaminomethylation of olefins [J].
Ahmed, M ;
Seayad, AM ;
Jackstell, R ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318
[2]   Direct Synthesis of Secondary Amines From Alcohols and Ammonia Catalyzed by a Ruthenium Pincer Complex [J].
Balaraman, Ekambaram ;
Srimani, Dipankar ;
Diskin-Posner, Yael ;
Milstein, David .
CATALYSIS LETTERS, 2015, 145 (01) :139-144
[3]   Mild and selective hydrogenation of aromatic and aliphatic (di) nitriles with a well-defined iron pincer complex [J].
Bornschein, Christoph ;
Werkmeister, Svenja ;
Wendt, Bianca ;
Jiao, Haijun ;
Alberico, Elisabetta ;
Baumann, Wolfgang ;
Junge, Henrik ;
Junge, Kathrin ;
Beller, Matthias .
NATURE COMMUNICATIONS, 2014, 5
[4]   TBAF-catalyzed hydrosilylation for the reduction of aromatic nitriles [J].
Bornschein, Christoph ;
Werkmeister, Svenja ;
Junge, Kathrin ;
Beller, Matthias .
NEW JOURNAL OF CHEMISTRY, 2013, 37 (07) :2061-2065
[5]   Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].
Buchwald, SL ;
Mauger, C ;
Mignani, G ;
Scholz, U .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39
[6]   Homogeneous Hydrogenation of Nitriles Catalyzed by Molybdenum and Tungsten Amides [J].
Chakraborty, Subrata ;
Berke, Heinz .
ACS CATALYSIS, 2014, 4 (07) :2191-2194
[7]   Iron-Based Catalysts for the Hydrogenation of Esters to Alcohols [J].
Chakraborty, Sumit ;
Dai, Huiguang ;
Bhattacharya, Papri ;
Fairweather, Neil T. ;
Gibson, Michael S. ;
Krause, Jeanette A. ;
Guan, Hairong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) :7869-7872
[8]   Tuneable Hydrogenation of Nitriles into Imines or Amines with a Ruthenium Pincer Complex under Mild Conditions [J].
Choi, Jong-Hoo ;
Prechtl, Martin H. G. .
CHEMCATCHEM, 2015, 7 (06) :1023-1028
[9]   REACTIONS OF ORTHO-BIS(DIMETHYLSILYL)BENZENE WITH NITRILES CATALYZED BY RHODIUM COMPLEXES [J].
CORRIU, RJP ;
MOREAU, JJE ;
PATAUDSAT, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 228 (03) :301-308
[10]   A General and Environmentally Benign Catalytic Reduction of Nitriles to Primary Amines [J].
Enthaler, Stephan ;
Addis, Daniele ;
Junge, Kathrin ;
Erre, Giulia ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (31) :9491-9494