Copper-Mediated One-Pot Synthesis of 2,2-Difluoro-1,3-benzoxathioles from o-Bromophenols and Trifluoromethanethiolate

Mengjia Zhang; Shouxiong Chen; Zhiqiang Weng

doi:10.1021/acs.orglett.7b03877

Copper-Mediated One-Pot Synthesis of 2,2-Difluoro-1,3-benzoxathioles from o-Bromophenols and Trifluoromethanethiolate

Org Lett. 2018 Jan 19;20(2):481-484. doi: 10.1021/acs.orglett.7b03877. Epub 2018 Jan 8.

Authors

Mengjia Zhang¹, Shouxiong Chen¹, Zhiqiang Weng¹

Affiliation

¹ State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University , Fujian 350108, China.

PMID: 29308902
DOI: 10.1021/acs.orglett.7b03877

Abstract

A copper-mediated difluoromethylenation of o-bromophenols with trifluoromethanethiolate is described. This one-pot protocol proceeds through an intermolecular addition of S=CF₂ (resulting from the decomposition of trifluoromethanethiolate) to o-bromophenols followed by intramolecular C-S coupling to form 2,2-difluoro-1,3-benzoxathioles. This method is compatible with a broad range of substrates and enables the late-stage difluoromethylenation of several functionally dense druglike o-bromophenols.

Publication types

Research Support, Non-U.S. Gov't