A direct reduction of aliphatic aldehyde, acyl chloride, ester, and carboxylic functions into a methyl group

被引:146
作者
Gevorgyan, V
Rubin, M
Liu, JX
Yamamoto, Y
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/jo001258a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aliphatic carboxylic group was efficiently reduced to the methyl group by HSiEt3 in the presence of catalytic amounts of B(C6F5)(3). To the best of our knowledge, this is the first example of a direct exhaustive reduction of aliphatic carboxylic function. Aliphatic aldehydes, acyl chlorides, anhydrides, and esters also underwent complete reduction under similar reaction conditions. Aromatic carboxylic acids, as well as other carbonyl functional equivalents, underwent smooth partial reduction to the corresponding TES-protected benzylic alcohols. It was shown that, unlike the reduction of aliphatic substrates, the exhaustive reduction of aromatic substrates was not straightforward: a concurrent Friedel-Crafts-like alkylation process competed with the reduction yielding trace to notable amounts of dimeric products, thus decreasing the overall selectivity of the reduction process.
引用
收藏
页码:1672 / 1675
页数:4
相关论文
共 22 条
[11]   A NEW FACILE DIASTEREOCONVERSION OF 2-AMINO ALCOHOLS INVOLVING A NOVEL CYCLOCARBAMATION [J].
KANO, S ;
YOKOMATSU, T ;
IWASAWA, H ;
SHIBUYA, S .
TETRAHEDRON LETTERS, 1987, 28 (50) :6331-6334
[12]   A HIGHLY STEREOCONTROLLED SYNTHETIC APPROACH TO VERSATILE MONOFLUORINATED MOLECULES [J].
KITAZUME, T ;
KOBAYASHI, T ;
YAMAMOTO, T ;
YAMAZAKI, T .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3218-3223
[13]   EFFICIENT METHOD FOR THE REDUCTIVE CLEAVAGE OF ACETALS AND KETALS WITH ZN(BH4)2/ME3SICL [J].
KOTSUKI, H ;
USHIO, Y ;
YOSHIMURA, N ;
OCHI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2594-2596
[14]  
LI GS, 1988, ORG SYNTH, V50-9, P747
[15]   CATALYSIS BY SOLID SUPERACIDS .20. NAFION-H CATALYZED REDUCTIVE CLEAVAGE OF ACETALS AND KETALS TO ETHERS WITH TRIETHYLSILANE [J].
OLAH, GA ;
YAMATO, T ;
IYER, PS ;
PRAKASH, GKS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2826-2828
[16]  
ORLOV NF, 1966, J GEN CHEM USSR, V36, P1078
[17]   Studies on the mechanism of B(C6F5)3-catalyzed hydrosilation of carbonyl functions [J].
Parks, DJ ;
Blackwell, JM ;
Piers, WE .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3090-3098
[18]   Tris(pentafluorophenyl)boron-catalyzed hydrosilation of aromatic aldehydes, ketones, and esters [J].
Parks, DJ ;
Piers, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9440-9441
[19]  
Pouchert C.J., 1993, Aldrich Library of 13C and 1H FT-NMR Spectra
[20]  
TSUNODA T, 1979, TETRAHEDRON LETT, P4679