TMSCl-Promoted Sulfonylation of Propargylic Alcohols with Sodium Sulfinates for the Construction of ()-1,3-Disulfonylpropenes and ()-1-Sulfonylpropenols.

A direct and novel transformation of propargylic alcohols with sodium sulfinates for the regio- and stereoselective synthesis of ()-1,3-disulfonylpropenes and ()-1-sulfonylpropenols was successfully developed in the presence of TMSCl under mild conditions. The preliminary mechanistic experiments demonstrated that the reaction underwent an unprecedented dual nucleophilic substitution/radical addition process, in which sodium sulfinates were used not only as nucleophiles but also as a sulfonyl radical source.