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Issue 54, 2016
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Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H

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Abstract

We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl–SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.

Graphical abstract: Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H

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Publication details

The article was received on 30 Mar 2016, accepted on 07 Jun 2016 and first published on 07 Jun 2016


Article type: Communication
DOI: 10.1039/C6CC02693A
Citation: Chem. Commun., 2016,52, 8448-8451
  • Open access: Creative Commons BY license
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    Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H

    J. L. Howard, C. Schotten, S. T. Alston and D. L. Browne, Chem. Commun., 2016, 52, 8448
    DOI: 10.1039/C6CC02693A

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