DOI: 10.1021/acs.orglett.6c03176 ISSN: 1523-7060

Visible Light Photoredox-Catalyzed Difunctionalization of (α-Substituted) N -Aryl Glycines with α-Bromoacetates: An Annulation Method for the Synthesis of 3-Substituted 2-Oxindoles via Decarboxylation/Ar

Zhengjiang Fu, Cheng Xiong, Chaopeng Luo, Qing Liu, Shengmei Guo, Hu Cai

Abstract

A novel and green approach for difunctionalization of (α-substituted) N-aryl glycines with α-bromoacetates via decarboxylation/aryl C–H activation was established under visible light photoredox catalysis. The protocol provided efficient access to desired products 3-substituted-2-oxindoles in moderate to excellent yields with good functional group tolerance. Mechanistic studies revealed that the transformation proceeded via a radical pathway with the aminomethyl and difluoromethyl radicals as key intermediates.

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