Triethylborane-induced radical allylation of α-halo carbonyl compounds with allylgallium reagent in aqueous media

被引：33

作者：

Usugi, S ^{[1
]}

Yorimitsu, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 27期

基金：

日本学术振兴会;

关键词：

allylation; radical reaction; solvents and solvent effects; gallium;

D O I：

10.1016/S0040-4039(01)00815-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An allylgallium reagent is found to be effective for radical allylation of alpha -iodo or alpha -bromo carbonyl compounds. Treatment of benzyl bromoacetate with allylgallium, prepared from allylmagnesium chloride and gallium trichloride, in the presence of triethylborane in THF provided benzyl 4-pentenoate in good yield. The addition of water as a cosolvent improved the yields of allylated products. It was revealed that the allylgallium species resists immediate decomposition on exposure to water. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4535 / 4538

页数：4

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