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Updated: Aug 26, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Divergent Construction of Heterocycles by SOMOphilic Isocyanide Insertion under N-Heterocyclic Carbene Catalysis
Qianrong Li1, Cong-Ying Zhou1, Chengming Wang1
1Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Department of Chemistry, Jinan University, Guangzhou, Guangdong 511443, China.
Abstract:
A variety of phenanthridines are rapidly constructed by an N-heterocyclic carbene (NHC)-catalyzed SOMOphilic isocyanide insertion-initiated homolytic aromatic substitution-type radical cyclization in the absence of any light, transition metals, and external oxidants. The aldehyde-free, scalable, and operationally simple protocol tolerates diverse functionalized biaryl isonitriles and activated α-halides. Moreover, it can be further applied to the divergent construction of other N-heterocycles. Preliminary mechanistic studies disclose that an NHC-derived radical cation intermediate is possibly involved.
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