Reduction of amides to amines via catalytic hydrosilylation by a rhodium complex

被引:157
作者
Kuwano, R [1 ]
Takahashi, M [1 ]
Ito, Y [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Div Synthet Chem & Biol Chem, Sakyo Ku, Kyoto 60601, Japan
关键词
D O I
10.1016/S0040-4039(97)10804-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol% of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with LiAlH4 and BH3. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1017 / 1020
页数:4
相关论文
共 18 条
[1]   MODELING THE PICHLER-SCHULZ MECHANISM BY CATALYTIC HYDROSILYLATION OF ACYL METAL-COMPLEXES [J].
AKITA, M ;
MITANI, O ;
MOROOKA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (09) :527-529
[2]   REDUCTION OF ACYL LIGAND IN TRANSITION-METAL COMPLEXES BY CATALYTIC HYDROSILYLATION [J].
AKITA, M ;
MITANI, O ;
SAYAMA, M ;
MOROOKA, Y .
ORGANOMETALLICS, 1991, 10 (05) :1394-1399
[3]   TITANOCENE-CATALYZED REDUCTION OF ESTERS USING POLYMETHYLHYDROSILOXANE AS THE STOICHIOMETRIC REDUCTANT [J].
BARR, KJ ;
BERK, SC ;
BUCHWALD, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4323-4326
[4]   REDUCTION OF AMIDES AND SILYL ESTERS WITH TRICHLOROSILANE-TERT-AMINES [J].
BENKESER, RA ;
LI, GS ;
MOZDZEN, EC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 178 (01) :21-28
[5]   A CATALYTIC METHOD FOR THE REDUCTION OF ESTERS TO ALCOHOLS [J].
BERK, SC ;
KREUTZER, KA ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5093-5095
[6]   AN AIR-STABLE CATALYST SYSTEM FOR THE CONVERSION OF ESTERS TO ALCOHOLS [J].
BERK, SC ;
BUCHWALD, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3751-3753
[7]   A mild general procedure for the one-pot conversion of amides to aldehydes [J].
Bower, S ;
Kreutzer, KA ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1515-1516
[8]  
BREEDEN SW, 1994, SYNLETT, P833
[9]  
Cavanaugh MD, 1996, ORGANOMETALLICS, V15, P2764
[10]   REDUCTION OF AMIDES AND LACTAMS TO AMINES BY REACTIONS WITH PHOSPHORUS OXYCHLORIDE AND SODIUM-BOROHYDRIDE [J].
KUEHNE, ME ;
SHANNON, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (12) :2082-2087