Photodecarboxylative Amination of Redox-Active Esters with Diazirines
Vishala Maharaj, Preeti P. Chandrachud, Wen Che, Łukasz Wojtas, Justin M. Lopchuk
Abstract
Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and nitrogen-containing heterocycles. Here, we report the photodecarboxylative amination of redox-active esters with diazirines using inexpensive photoactivators under mild conditions with an enhanced scope for primary substrates. The stability of diazirines to blue light is demonstrated, paving the way for further research into other photochemical amination methods with these unique heterocycles.
Topics & Concepts
ChemistryAminationElectrophilic aminationReagentReductive aminationCombinatorial chemistryRedoxElectrophilePrimary (astronomy)Organic chemistryPhotochemistryCatalysisPhysicsAstronomySynthesis and Catalytic ReactionsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques