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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A method for the preparation of aryl α,α-difluoroethyl thioethers (ArSCF2CH3) is reported and the synthesis approach is extended to aryl alpha,alpha-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.
Tomita , R , Al-Maharik , N , Rodil , A , Buhl , M & O'Hagan , D 2018 , ' Synthesis of aryl α,α-difluoroethyl thioethers a novel structure motif in organic chemistry, and extending to aryl α,α-difluoro oxyethers ' Organic & Biomolecular Chemistry , vol. 16 , no. 7 , pp. 1113-1117 . DOI: 10.1039/c7ob02987j
Organic & Biomolecular Chemistry
© 2018 the Authors. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/ 10.1039/C7OB02987J
DescriptionThe authors thank the Marie Curie ITN programme for Funding (AR).
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