Intramolecular Nonbonded Se···F Interaction-Promoted SuFEx Click Chemistry for the Synthesis of β-Selenyl Sulfonates and Sulfonamides

An intramolecular nonbonded Se···F interaction-promoted SuFEx click platform has been developed for the modular synthesis of valuable β-selenyl sulfonates and sulfonamides using readily available selenols, ethenesulfonyl fluoride (ESF) and diverse O - and N -nucleophiles. Upon Michael addition of selenols to ESF, the relatively inert sulfonyl group on ESF will become activated via intramolecular nonbonded Se···F interactions, which enables it to react with various O - and N -nucleophiles under mild conditions. In this reaction, the embedded selenium atom plays a dual role by promoting the latent alkyl SuFEx process through Se···F interaction and being retained as a valuable motif in the final products.