Visible-Light-Driven Nitrogen Radical-Catalyzed [3 + 2] Cyclization of Vinylcyclopropanes and N -Tosyl Vinylaziridines with Alkenes

作者：Quanqing Zhao, Xue‐Song Zhou, Shuang-Hua Xu, Yali Wu, Wen‐Jing Xiao, Jia‐Rong Chen · 发表于：Organic Letters · 年份：2020 · DOI：10.1021/acs.orglett.0c00712 · 被引用次数：67 · 研究领域：Catalytic C–H Functionalization Methods、Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques

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.