Convenient One-Pot Synthesis of (E)-β-Aryl Vinyl Halides from Benzyl Bromides and Dihalomethanes

被引：54

作者：

Bull, James A. ^{[1
]}

Mousseau, James J. ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 23期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1021/ol802315k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)-beta-Aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide (E)-beta-aryl vinyl chlorides and bromides by employing the anions of ICH2CI or CH2Br2. The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides.

引用

页码：5485 / 5488

页数：4

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