An efficient synthesis of benzyl bromides from aromatic aldehydes using polymethylhydrosiloxane and (bromodimethyl)sulfonium bromide or N-bromosuccinimide

被引：26

作者：

Das, Biswanath ^{[1
]}

Srinivas, Yallamalla ^{[1
]}

Holla, Harish ^{[1
]}

Laxminarayana, Keetha ^{[1
]}

Narender, Ravirala ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 38期

关键词：

polymethylhydrosiloxane (PMHS); (bromodimethyl)sulfonium bromide; NBS; aromatic aldehydes; benzylic bromide;

D O I：

10.1016/j.tetlet.2007.07.125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymethylhydrosiloxane (PMHS) in combination with (bromodimethyl)sulfonium bromide or NBS has been utilized for the first time for reductive bromination of aromatic aldehydes at room temperature to afford the corresponding benzyl bromides in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6681 / 6683

页数：3

共 6 条

[1] REDUCTION OF CARBONYL-COMPOUNDS PROMOTED BY SILICON HYDRIDES UNDER THE INFLUENCE OF TRIMETHYLSILYL-BASED REAGENTS [J].

AIZPURUA, JM ;

LECEA, B ;

PALOMO, C .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (12) :2342-2347

[2] An expedient stereoselective synthesis of (Z)- and (E)-ally iodides from Baylis-Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane-iodine system [J].

Das, Biswanath ;

Holla, Harish ;

Srinivas, Yallamalla ;

Chowdhury, Nikhil ;

Bandgar, B. P. .

TETRAHEDRON LETTERS, 2007, 48 (18) :3201-3204

[3]

FURUKAWA N, 1973, J CHEM SOC CHEM COMM, P212

[4] A simple and practical synthetic protocol for acetalisation, thioacetalisation and transthioacetalisation of carbonyl compounds under solvent-free conditions [J].

Khan, AT ;

Mondal, E ;

Ghosh, S ;

Islam, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (09) :2002-2009

[5] Polymethylhydrosiloxane: a versatile reducing agent for organic synthesis [J].

Lawrence, NJ ;

Drew, MD ;

Bushell, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (23) :3381-3391

[6]

OLAH GA, 1979, SYNTHESIS-STUTTGART, P720

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