New sulfuryl fluoride-derived alkylating reagents for the 1, 1-dihydrofluoroalkylation of thiols. Issue 44 (27th September 2019)

• Record Type: Journal Article
• Authors: Foth, Paul J.; Gu, Frances; Bolduc, Trevor G.; Kanani, Sahil S.; Sammis, Glenn M.
• Is Part Of: Chemical science. Volume 10:Issue 44(2019)
• Page Start: 10331
• Page End: 10335
• Publication Date: 2019-09-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc03570b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Herein, we report a new method for the one-pot synthesis of 1, 1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2 F2 ) through a solution of the corresponding alcohol and thiol. Abstract : Herein, we report a new method for the one-pot synthesis of 1, 1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2 F2 ) 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.