Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate

被引:52
作者
Bhanushali, Mayur J. [1 ]
Nandurkar, Nitin S. [1 ]
Bhor, Malhari D. [1 ]
Bhanage, Bhalchandra M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India
关键词
reductive animation; bis(triphenylphosphine) copper(I) tetrahydroborate; carbonyl compounds; amines;
D O I
10.1016/j.tetlet.2006.12.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct reductive amination protocol for a Idehydes/ket ones using bis(triphenylphosphine) copper(I) tetrahyd rob orate as a novel reducing agent in the presence of sulfamic acid has been developed. The reagent chemoselectively reduces the imine moiety and does not affect other reducible functionalities such as chloro, nitro, cyano and methoxy. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1273 / 1276
页数:4
相关论文
共 27 条
[1]   Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].
AbdelMagid, AF ;
Carson, KG ;
Harris, BD ;
Maryanoff, CA ;
Shah, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862
[2]   USE OF ZINC BOROHYDRIDE IN REDUCTIVE AMINATION - AN EFFICIENT AND MILD METHOD FOR N-METHYLATION OF AMINES [J].
BHATTACHARYYA, S ;
CHATTERJEE, A ;
DUTTACHOWDHURY, SK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01) :1-2
[3]   A MILD, PYRIDINE-BORANE-BASED REDUCTIVE AMINATION PROTOCOL [J].
BOMANN, MD ;
GUCH, IC ;
DIMARE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5995-5996
[4]   CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].
BORCH, RF ;
BERNSTEIN, MD ;
DURST, HD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+
[5]   PREPARATION OF DIAMINO ETHERS AND POLYAMINES [J].
BRADSHAW, JS ;
KRAKOWIAK, KE ;
IZATT, RM .
TETRAHEDRON, 1992, 48 (22) :4475-4515
[6]   MAGNESIUM-ION MEDIATED STEREOSPECIFIC FORMATION OF N-SUBSTITUTED ETHANOLAMINES DURING REDUCTIVE AMINATION [J].
BRUSSEE, J ;
VANBENTHEM, RATM ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON-ASYMMETRY, 1990, 1 (03) :163-166
[7]  
Emerson W. S., 1948, ORG REACTIONS, V4, P174
[8]   BIS(TRIPHENYLPHOSPHINE)COPPER (I) TETRAHYDROBORATE IN THE REDUCTION OF P-TOLUENESULFONYLHYDRAZONES AND 2,4,6-TRIISOPROPYLBENZENESULPHONYL HYDRAZONES (TRISYL HYDRAZONES) TO ALKANES [J].
FLEET, GWJ ;
HARDING, PJC ;
WHITCOMBE, MJ .
TETRAHEDRON LETTERS, 1980, 21 (41) :4031-4034
[9]  
FLEET GWJ, 1979, TETRAHEDRON LETT, V20, P975
[10]   APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].
GORDON, EM ;
BARRETT, RW ;
DOWER, WJ ;
FODOR, SPA ;
GALLOP, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401