Trichlorosilane-dimethylformamide (Cl3SiH-DMF) as an efficient reducing agent. Reduction of aldehydes and imines and reductive amination of aldehydes under mild conditions using hypervalent hydridosilicates

被引:163
作者
Kobayashi, S
Yasuda, M
Hachiya, I
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
关键词
D O I
10.1246/cl.1996.407
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Trichlorosilane-dimethylformamide (Cl3SiH-DMF) was found to be an effective reducing agent for reduction of aldehydes to alcohols, imines to amines, and also reductive amination of aldehydes. Hypervalent silicates are active species, which enable efficient reduction under mild conditions.
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页码:407 / 408
页数:2
相关论文
共 15 条
[1]   REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE [J].
ABDELMAGID, AF ;
MARYANOFF, CA ;
CARSON, KG .
TETRAHEDRON LETTERS, 1990, 31 (39) :5595-5598
[2]   A NEW METHOD OF FORMING CARBON-SILICON BOND . REDUCTIVE SILYLATION OF CARBONYL COMPOUNDS [J].
BENKESER, RA ;
SMITH, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1556-&
[3]   TRICHLOROSILANE-IMINE COMPLEXES - A NEW METHOD FOR THE REDUCTION OF IMINES TO AMINES [J].
BENKESER, RA ;
SNYDER, DC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 225 (01) :107-115
[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]   SI-29 NMR OF 5-COORDINATE AND 6-COORDINATE ORGANO-SILICON COMPLEXES [J].
CELLA, JA ;
CARGIOLI, JD ;
WILLIAMS, EA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 186 (01) :13-17
[6]   REACTIVITY OF HYPERVALENT SPECIES OF SILICON - CLEAVAGE OF THE ALLYL SILICON BOND [J].
CERVEAU, G ;
CHUIT, C ;
CORRIU, RJP ;
REYE, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 328 (03) :C17-C20
[7]   FLUORIDE-ION CATALYZED REDUCTION OF ALDEHYDES AND KETONES WITH HYDROSILANES - SYNTHETIC AND MECHANISTIC ASPECTS AND AN APPLICATION TO THE THREO-DIRECTED REDUCTION OF ALPHA-SUBSTITUTED ALKANONES [J].
FUJITA, M ;
HIYAMA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5405-5415
[8]   STUDIES ON ORGANOSILICON CHEMISTRY .100. PENTACOORDINATE ALLYLSILICONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF TRIETHYLAMMONIUM BIS(CATECHOLATO)ALLYLSILICONATES AND SELECTIVE ALLYLATION OF ALDEHYDES [J].
HOSOMI, A ;
KOHRA, S ;
OGATA, K ;
YANAGI, T ;
TOMINAGA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2415-2420
[9]  
HUDLICKY M, 1984, REDUCTION ORGANIC CH
[10]  
KIRA M, 1987, Journal of Organic Chemistry, V52, P949