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New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols

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Abstract

Herein, we report a new method for the one-pot synthesis of 1,1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2F2) through a solution of the corresponding alcohol and thiol. The reaction proceeds through a new class of bis(1,1-dihydrofluoroalkyl) sulfate reagents, to afford the desired 1,1-dihydrofluoroalkyl sulfides in 55–90% isolated yields. The bis(1,1-dihydrofluoroalkyl) sulfates are highly chemoselective for thiol alkylation, and are unreactive with competing, unprotected nucleophiles, including amines, alcohols, and carboxylic acids.

Graphical abstract: New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols

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Publication details

The article was received on 19 Jul 2019, accepted on 19 Sep 2019 and first published on 20 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03570B
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols

    P. J. Foth, F. Gu, T. G. Bolduc, S. S. Kanani and G. M. Sammis, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03570B

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