通过硫原子上的均裂取代反应，由4-戊炔基硫醚无锡生成烷基自由基。

Tin-free generation of alkyl radicals from alkyl 4-pentynyl sulfides via homolytic substitution at the sulfur atom.

作者信息

Bencivenni Giorgio, Lanza Tommaso, Leardini Rino, Minozzi Matteo, Nanni Daniele, Spagnolo Piero, Zanardi Giuseppe

机构信息

Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy.

出版信息

Org Lett. 2008 Mar 20;10(6):1127-30. doi: 10.1021/ol800046k. Epub 2008 Feb 16.

DOI:10.1021/ol800046k

PMID:18278931

Abstract

Homolytic substitution at the sulfur atom of beta-(phenylsulfanyl)vinyl radicals, obtained by radical reaction of benzenethiol with easily accessible alkyl 4-pentynyl sulfides, is a mild, effective, tin-free route for the generation of all types of alkyl radicals. This protocol can be employed in reductive defunctionalizations as well as cyclizations onto both electron-rich and electron-poor C-C double bonds.

摘要

通过苯硫酚与易于获得的烷基4-戊炔基硫醚发生自由基反应得到的β-(苯硫基)乙烯基自由基在硫原子上的均裂取代反应，是一种温和、有效的无锡方法，可用于生成各种类型的烷基自由基。该方法可用于富电子和缺电子的C-C双键的还原脱官能化反应以及环化反应。