Iron-Catalyzed Sulfonylthiocyanation of α,β-Unsaturated Amides/Esters via the Insertion of Sulfur Dioxide

An iron-catalyzed four-component sulfonylthiocyanation between alpha,beta-unsaturated amides/esters, TMSNCS, aryldiazonium tetrafluoroborates, and sulfur dioxide (from SOgen) is demonstrated. This protocol is characterized by mild reaction conditions, good functional group compatibility, broad substrate scope, and good to excellent yields, providing a feasible method for the preparation of beta-thiocyanated sulfone compounds. The preliminary mechanism investigation shows that a radical pathway may be involved in the process.

Automated summary

An iron-catalyzed four-component sulfonylthiocyanation reaction has been demonstrated, providing a feasible method for the preparation of beta-thiocyanated sulfone compounds. The reaction conditions are mild, with good functional group compatibility and broad substrate scope. Preliminary mechanistic investigation suggests the involvement of a radical pathway.