Symbiotic Transition‐Metal and Organocatalysis for Catalytic Ambient Amine Oxidation and Alkene Reduction Reactions

Abstract

Abstract A new oxidation reaction based on two simple catalysts, namely, alloxan and a Cu I salt, is highly effective for the aerobic oxidation and oxidative cross‐coupling of amines. The reaction is operationally simple, reaction atmospheres enriched in dioxygen are obviated, and neither catalyst component requires prior synthesis. Mechanistic investigations have been performed and point towards a complex reaction manifold with evidence that supports a catalytic cycle that does not proceed through a quinone‐imine step. Additionally, this dual catalyst system is efficient to effect diimide‐mediated hydrogenation reactions of alkenes and alkynes, a transformation that has not been reported previously in the context of quinone catalyst systems.