Divergent Construction of Heterocycles by SOMOphilic Isocyanide Insertion under N-Heterocyclic Carbene Catalysis
Qianrong Li, Cong‐Ying Zhou, Chengming Wang
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.
Topics & Concepts
ChemistryCarbeneHomolysisIsocyanideCatalysisCombinatorial chemistryDivergent synthesisHalideOrganic chemistryRadicalCatalytic C–H Functionalization MethodsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling Reactions