Iron-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Terminal Alkynes with Aromatic Sulfonyl Chlorides

被引：103
|
作者：
Zeng, Xiaoming [1 ]
Ilies, Laurean [1 ]
Nakamura, Eiichi [1 ]
机构：
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 03期
基金：
日本学术振兴会;
关键词：
BETA-CHLOROVINYL SULFONES; H BOND ACTIVATION; GRIGNARD-REAGENTS; TETRASUBSTITUTED ALKENES; ACETYLENES; OLEFINS; ARYLATION; HALIDES; AGE;
D O I：
10.1021/ol203446t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Terminal alkynes react with aromatic sulfonyl chlorides in the presence of an iron(II) catalyst and a phosphine ligand to give (E)-beta-chlorovinylsulfones with 100% regio- and stereoselectivity. Various functional groups, such as chloride, bromide, iodide, nitro, ketone, and aldehyde, are tolerated under the reaction conditions. Addition of tosyl chloride to a 1,6-enyne followed by radical 5-exo-trig cyclization gave an exocyclic alkenylsulfone.
引用
收藏
页码：954 / 956
页数：3
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