Water-mediated transition-metal-free Tsuji-Trost-type reaction

被引：28

作者：

Chevrin, C ^{[1
]}

Le Bras, J ^{[1
]}

Hénin, F ^{[1
]}

Muzart, J ^{[1
]}

机构：

[1] Univ Reims, CNRS, Unite Mixte Rech React Select & Applicat, F-51687 Reims 2, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 44期

关键词：

water chemistry; allylic acetate; substitution; palladium; B(AL)1-SN1; mechanism;

D O I：

10.1016/j.tetlet.2003.09.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of 1-acetoxy-1,3-diphenylpropene (1) by C-, O-, S- and N-nucleophiles in basic aqueous media produced the corresponding substitution products in the absence of a transition-metal catalyst. Mechanistic studies, using (S)-1 and p-MeC6H4CH(OAc)CH=CHPh as substrates, led to propose a B(AL)1 cleavage of the ester function leading to a stabilized allylic carbocation as intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8099 / 8102

页数：4

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