Issue 72, 2024

Thionyl fluoride as a sulfur(iv) SuFEx hub for the efficient syntheses of sulfinamides and sulfinate esters

Abstract

Herein, we demonstrate a method for the syntheses of sulfinamides and sulfinate esters using a novel sulfur(IV) fluoride exchange reaction with organometallic reagents. Our strategy involves the addition of an amine or alcohol nucleophile to thionyl fluoride, acting as a S(IV) SuFEx hub, followed by an organometallic reagent. This approach allows efficient access to sulfinamides (45–91% yields) and sulfinate esters (44–82% yields) in only 30 minutes. The sulfinamide and sulfinate esters also can be readily derivatized to the corresponding S(VI) sulfonamides, sulfonate esters, sulfonimidamides, and sulfonimidates without isolation of the intermediates.

Graphical abstract: Thionyl fluoride as a sulfur(iv) SuFEx hub for the efficient syntheses of sulfinamides and sulfinate esters

Supplementary files

Article information

Article type
Communication
Submitted
14 Jun 2024
Accepted
08 Aug 2024
First published
09 Aug 2024

Chem. Commun., 2024,60, 9765-9768

Thionyl fluoride as a sulfur(IV) SuFEx hub for the efficient syntheses of sulfinamides and sulfinate esters

W. P. Chappell, M. Favié and G. M. Sammis, Chem. Commun., 2024, 60, 9765 DOI: 10.1039/D4CC02876G

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