Reduction of carbonyl function to a methyl group

被引：41

作者：

Bajracharya, GB

Nogami, T

Jin, T

Matsuda, K

Gevorgyan, V

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[2] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

SYNTHESIS-STUTTGART | 2004年 / 02期

关键词：

reductions; aldehydes; acyl chlorides; esters; carboxylic acids;

D O I：

10.1055/s-2003-44356

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct exhaustive reduction of aliphatic carbonyl functions (aldehydes, acyl chlorides, esters and carboxylic acids) to a methyl group by triethylsilane (Et3SiH) in the presence of catalytic amount of tris(pentafluorophenyl)borane [B(C6F5)(3)] is described. Aromatic carbonyl functions could undergo partial reduction to the corresponding TES-protected benzylic alcohols.

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收藏

页码：308 / 311

页数：4

相关论文

共 30 条

[1]

[Anonymous], REDUCTIONS ALUMINO B

[2]

[Anonymous], ADV ORGANIC CHEM

[3] A NEW AND CONVENIENT METHOD FOR REDUCTION OF AN AROMATIC CARBOXYL TO A METHYL GROUP [J].

BENKESER, RA ;

FOLEY, KM ;

GAUL, JM ;

LI, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3232-&

[4] B(C6F5)3-catalyzed silation of alcohols:: A mild, general method for synthesis of silyl ethers [J].

Blackwell, JM ;

Foster, KL ;

Beck, VH ;

Piers, WE .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4887-4892

[5] Rapid defunctionalization of carbonyl group to methylene with polymethylhydrosiloxane-B(C6F5)3 [J].

Chandrasekhar, S ;

Reddy, CR ;

Babu, BN .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :9080-9082

[6] Concerning a general method regarding the reduction of the carbonyl group in aldehydes and ketones to methylene groups (III Announcement) [J].

Clemmensen, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1914, 47 :681-687

[7] On a general method of the reduction of the carbonyl group in aldehydes and ketones of the methylene group [J].

Clemmensen, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1914, 47 :51-63

[8] A NEW SYNTHETIC ROUTE TO (+/-)-STRIGOL [J].

DAILEY, OD .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :1984-1989

[9] SILANE REDUCTIONS IN ACIDIC MEDIA .8. BORON-TRIFLUORIDE CATALYZED ORGANOSILANE REDUCTIONS, SELECTIVITY AND MECHANISM [J].

DOYLE, MP ;

WEST, CT ;

DONNELLY, SJ ;

MCOSKER, CC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 117 (02) :129-140

[10] A direct reduction of aliphatic aldehyde, acyl chloride, ester, and carboxylic functions into a methyl group [J].

Gevorgyan, V ;

Rubin, M ;

Liu, JX ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1672-1675