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Updated: May 30, 2025

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
Bromide-promoted cascade annulation of isocyanobiaryls with aldehydes through photoredox catalysis
Mengran Gan1, Xiaoting Wu1, Xiaochen Ji1,2
1Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China. xcji@xtu.edu.cn.
Abstract:
Herein, we report a cascade annulation of readily available isocyanobiaryls with simple aldehydes via photoredox catalysis, providing a straightforward approach towards valuable 6-hydroxyalkylated phenanthridines. Mechanistic studies indicated the generation of a key acyl radical from aldehydes by hydrogen atom abstraction with a bromine radical. This protocol exhibits exceptional chemoselectivity, excellent tolerance of various functional groups and mild reaction conditions. Its synthetic utility was demonstrated by a gram-scale reaction and various facile manipulations of the free hydroxyl group to furnish diverse phenanthridine derivatives.
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