Visible-Light-Driven Nitrogen Radical-Catalyzed [3 + 2] Cyclization of Vinylcyclopropanes and <i>N</i>-Tosyl Vinylaziridines with Alkenes
Quanqing Zhao, Xue‐Song Zhou, Shuang-Hua Xu, Yali Wu, Wen‐Jing Xiao, Jia‐Rong Chen
Abstract
A visible light photoredox-promoted and nitrogen radical catalyzed [3 + 2] cyclization of vinylcyclopropanes and N-tosyl vinylaziridines with alkenes is developed. Key to the success of this process is the use of the readily tunable hydrazone as a nitrogen radical catalyst. Preliminary mechanism studies suggest that the photogenerated nitrogen radical undergoes reversible radical addition to the vinylcyclopropanes and N-tosyl vinylaziridines to enable their ring-opening C–C and C–N bond cleavage and ensuing cyclization with alkenes.
Topics & Concepts
ChemistryTosylCatalysisNitrogenMedicinal chemistryCombinatorial chemistryPhotochemistryOrganic chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques