NHC–Boryl Radical-Catalyzed [3 + 2] Cycloaddition for the Synthesis of Vinylcyclopentanes

作者：Yee Lin Phang, Yan Liu, Jie Wang, Ji‐Kang Jin, Yi‐Feng Wang · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.5c02138 · 被引用次数：2 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Organoboron and organosilicon chemistry

Heteroatom-centered radicals have recently found important applications in catalyzing a series of radical transformations. Herein, we report a benzimidazolium-based N -heterocyclic carbene (NHC)-boryl radical-catalyzed [3 + 2] cycloaddition between vinylcyclopropanes and alkenes. Such a covalent radical catalysis process features radical addition, cyclopropane ring opening, intermolecular radical addition, ring cyclization, and radical elimination steps to deliver vinylcyclopentanes with good yields and substrate scope.