Blue LED-Driven Synthesis of Benzoyl-Guanidine Hybrids via Radical-Radical Cross-Coupling

Abstract

We describe a radical-radical coupling strategy for guanylation of benzoyl-thiourea derivatives, with diverse secondary amines to afford bioactive benzoyl-guanidine hybrids under blue LED irradiation in a greener reaction media. Moreover, this effective, high atom-economy (90%) protocol involves molecular cleavage (via Mumm rearrangement), formation of revised fragments, and reassembly of selective radical fragments. In addition, the work demonstrates postmodification of the benzoyl guanidine to bioactive isoquinolinone scaffolds via ruthenium-catalyzed oxidative annulation with diphenylacetylene.