Copper-Mediated One-Pot Synthesis of 2,2-Difluoro-1,3-benzoxathioles from o‑Bromophenols and Trifluoromethanethiolate
journal contributionposted on 08.01.2018 by Mengjia Zhang, Shouxiong Chen, Zhiqiang Weng
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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.