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
收藏
页码：8099 / 8102
页数：4
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