Anode-induced arylthiol-amine cross-coupling: A nontraditional strategy to access sulfinamides.

Abstract

Sulfinamides are ubiquitous structures among natural products and biologically active compounds. Generic synthetic methods for sulfinamides remain elusive because the preparation of sulfoxide precursors is notoriously difficult. Direct construction of S─N bonds represents a highly efficient economical method to access these sulfinamides. However, the most prevalent techniques for their synthesis are still the nonradical approaches of sulfoxide precursors with amines, where prepreparation of substrates, harsh reaction conditions, and restricted substrate ranges have intrinsically limited the synthetic scope. Herein, we leveraged a practical and streamlined electrocatalytic strategy to achieve sulfinamide synthesis, which involves the intermolecular oxidative cross-coupling of readily available arylthiols and aliphatic amines. Mechanistic investigations indicate that four successive oxidations at the anode play a crucial role in radical generation, S─N bond formation, and further oxidation of intermediates.