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Visible-light-induced radical cascade reaction to prepare oxindoles via alkyl radical addition to N-arylacryl amides†
Hanchao Cheng,Yunfeng Luo,Tsz-Lung Lam,Yungen Liu
Organic Chemistry Frontiers Pub Date : 09/26/2022 00:00:00 , DOI:10.1039/D2QO01140A
Abstract

Herein we describe a photochemical approach towards oxindoles by the radical cascade reaction of α,β-unsaturated N-arylacryl amides with alkyl bromides or iodides upon visible light irradiation. This transition metal- and photosensitizer-free protocol afforded diverse oxindoles with C3 quaternary centers in high product yields under mild reaction conditions. Importantly, the method was applicable to prepare the core skeletons of (±)-physovenine, (±)-esermethole and (±)-physostigmine.

Graphical abstract: Visible-light-induced radical cascade reaction to prepare oxindoles via alkyl radical addition to N-arylacryl amides
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