A catalytic intramolecular nitrene insertion into a copper(i)–N-heterocyclic carbene bond yielding fused nitrogen heterocycles†
Kévin Fauché,Lionel Nauton,Laurent Jouffret,Federico Cisnetti,Arnaud Gautier
Chemical Communications Pub Date : 01/31/2017 00:00:00 , DOI:10.1039/C6CC09160A
Abstract

N-(2-Azidophenyl)azolium salts were easily prepared and reacted with copper(I) under conditions allowing the formation of NHC complexes. Under these conditions, the formation of benzimidazo-fused heterocycles occurred under catalytic, efficient and very mild conditions. This reaction is proposed to proceed via dinitrogen elimination and imido/nitrene–NHC cyclization.

Graphical abstract: A catalytic intramolecular nitrene insertion into a copper(i)–N-heterocyclic carbene bond yielding fused nitrogen heterocycles