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

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页码：954 / 956

页数：3

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