Thionyl Fluoride as a Sulfur(IV) SuFEx Hub for the Efficient Syntheses of Sulfinamides and Sulfinate Esters

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.