Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis with a Catalytic Amount of Silane Reagent
journal contributionposted on 25.03.2021, 12:34 authored by Xiao-Yu Zhang, Xiao-Yun Wu, Bo Zhang, Yin Wei, Min Shi
A silyl radical-mediated carbocyclization of acrylamide-/vinyl sulfonamide-attached alkylidenecyclopropanes via photoredox catalysis with a catalytic amount of silane reagent is reported in this paper. With this protocol, a highly efficient synthesis for the construction of lactam- and sultam-containing polycyclic derivatives in 63–95% yields was achieved with a broad substrate scope. A reasonable reaction mechanism was proposed based on control experiments, where the catalytic amount of tris(trimethylsilyl)silane was used as the radical-based reagent.
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Sulfonamide-Attachedreaction mechanismSilyl Radical-Mediated Carbocyclizationyieldsilane reagentAcrylamidecontrol experimentstrisalkylidenecyclopropaneCatalytic AmountPhotoredox Catalysissynthesissilyl radical-mediated carbocyclizationconstructionSilane Reagentlactamsubstrate scopeacrylamideAlkylidenecyclopropanesultam-containing polycyclic deriva...radical-based reagentphotoredox catalysissulfonamide-attached