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

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.

SUBMITTER: Foth PJ

PROVIDER: S-EPMC6984387 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Foth Paul J PJ Gu Frances F Bolduc Trevor G TG Kanani Sahil S SS Sammis Glenn M GM

Chemical science 20190920 44

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 comp ...[more]

PMID: 32110320

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