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Issue 7, 2018
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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

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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.

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

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Publication details

The article was received on 03 Dec 2017, accepted on 10 Jan 2018 and first published on 10 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02987J
Citation: Org. Biomol. Chem., 2018,16, 1113-1117
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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

    R. Tomita, N. Al-Maharik, A. Rodil, M. Bühl and D. O'Hagan, Org. Biomol. Chem., 2018, 16, 1113
    DOI: 10.1039/C7OB02987J

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