Transition-Metal-Free, Visible-Light-Driven Regioselective Phosphinoylation/Hydrazonation of Unactivated Alkenes with Arylhydrazines and H-Phosphine Oxides
Weifeng Xu , Minjing Yuan , Longzhi Zhu , Sha Jin , Biquan Xiong
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (21) : 2787 -2794.
Transition-Metal-Free, Visible-Light-Driven Regioselective Phosphinoylation/Hydrazonation of Unactivated Alkenes with Arylhydrazines and H-Phosphine Oxides
A novel visible-light-driven protocol has been established for the direct difunctionalization of unactivated alkenes using arylhydrazines and H-phosphine oxides as dual-function reagents. Through visible-light photocatalysis, phosphonyl radicals are generated as key intermediates, which undergo a cascade process involving radical addition, single-electron oxidation, and dehydration coupling to achieve the in-situ construction of C–P and C=N–N bonds. The method demonstrates broad substrate compatibility with excellent functional group tolerance, delivering β-phosphinoyl hydrazones in moderate to good yields. Notably, several synthesized compounds exhibit potent anti-proliferative activity against HepG2 cells. Mechanistic investigations through radical trapping experiments and kinetic studies confirm a radical chain pathway, with photocatalysis crucially mediating the initial radical generation and subsequent electron transfer processes.
Photocatalysis / Alkenes / Difunctionalization / Radicals / Transition-metal-free / Phosphinoylation / Hydrazonation
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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