Transition-Metal-Free, Visible-Light-Driven Regioselective Phosphinoylation/Hydrazonation of Unactivated Alkenes with Arylhydrazines and H-Phosphine Oxides
Weifeng Xu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Minjing Yuan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
E-mail: [email protected]; [email protected]Search for more papers by this authorLongzhi Zhu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorSha Jin
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Biquan Xiong
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China
E-mail: [email protected]; [email protected]Search for more papers by this authorWeifeng Xu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Minjing Yuan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
E-mail: [email protected]; [email protected]Search for more papers by this authorLongzhi Zhu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorSha Jin
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Biquan Xiong
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
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.
Supporting Information
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