Synthesis of aryl α,α-difluoroethyl thioethers a novel structure motif in organic chemistry, and extending to aryl α,α-difluoro oxyethers†,10.1039/C7OB02987J

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Synthesis of aryl α,α-difluoroethyl thioethers a novel structure motif in organic chemistry, and extending to aryl α,α-difluoro oxyethers†

Nawaf Al-Maharik,Andrea Rodil,Michael Bühl,David O'Hagan

Organic & Biomolecular Chemistry Pub Date : 01/10/2018 00:00:00 , DOI:10.1039/C7OB02987J

Abstract

A method for the preparation of aryl α,α-difluoroethyl thioethers (ArSCF₂CH₃) is reported and the synthesis approach is extended to aryl α,α-difluoroethyl oxygen ethers. Selected building blocks are further elaborated in cross-coupling reactions and are incorporated into analogues of established trifluoromethyl ether drugs. Conformations are explored and log P studies of these motifs indicate that they are significantly more polar than their trifluoromethyl ether analogues rendering them attractive for bioactives discovery.