Visible‐Light‐Induced Oxidation of Diazenyl‐Protected Tetrahydroisoquinolines and Isoindolines for the Synthesis of Functionalized Lactams
Tao Zhang, Yanhong Wang, Bin Wang, Weiwei Jin, Yu Xia, Chenjiang Liu, Yonghong Zhang
Abstract
Abstract A visible‐light‐induced oxidation of diazenyl‐protected tetrahydroisoquinolines and isoindolines for the synthesis of structurally diverse lactams is developed. The reaction was carried out with Eosin Y‐Na 2 as an organic photocatalyst and molecular oxygen as an oxidant, and the desired functionalized N ‐aryldiazenyl‐lactams were obtained under mild and transition metal‐free conditions. The utility of this method is showcased by the gram‐scale synthesis and deprotection of the N ‐aryldiazenyl‐lactam product. magnified image
Topics & Concepts
ChemistryVisible spectrumEosin YCombinatorial chemistryLactamStereochemistryPhotocatalysisCatalysisOrganic chemistryOptoelectronicsPhysicsOxidative Organic Chemistry ReactionsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods