Visible-Light-Driven Aryl Migration and Cyclization of α-Azido Amides
Siyu Liang, Kai‐Jie Wei, Yajun Lin, Tuming Liu, Dian Wei, Bing Han, Wei Yu
Abstract
This paper reports two new visible-light-promoted radical reactions of α-azido amides. By catalysis of [Ir(ppy)2(dtbbpy)]PF6 with i-Pr2NEt as the reducing agent, N-aryl α-azido tertiary amides were first converted to the corresponding aminyl radicals through reduction of the azido group; the aminyl radicals then underwent N-to-N aryl migration to give α-anilinyl-functionalized amides. α-Azido secondary amides, on the other hand, reacted with the solvent ethanol and i-Pr2NEt to afford the imidazolinone products.
Topics & Concepts
ChemistryRadicalArylEthanolAryl radicalSolventVisible spectrumCatalysisPhotochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryOptoelectronicsAlkylPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques