Radical (phenylsulfonyl)difluoromethylation with iododifluoromethyl phenyl sulfone

Ya Li; Jun Liu; Laijun Zhang; Lingui Zhu; Jinbo Hu

doi:10.1021/jo070618s

Radical (phenylsulfonyl)difluoromethylation with iododifluoromethyl phenyl sulfone

J Org Chem. 2007 Jul 20;72(15):5824-7. doi: 10.1021/jo070618s. Epub 2007 Jun 23.

Authors

Ya Li¹, Jun Liu, Laijun Zhang, Lingui Zhu, Jinbo Hu

Affiliation

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

PMID: 17590048
DOI: 10.1021/jo070618s

Abstract

An unprecedented radical (phenylsulfonyl)difluoromethylation of terminal alkenes with PhSO2CF2I has been achieved by using Et3B/air as an initiator. This synthetic methodology was also used in the one-pot regioselective preparation of PhSO2CF2-substituted alkanes, and in the regio- and stereoselective preparation of PhSO2CF2-substituted alkenes with high E/Z ratio (up to > or =100:1).