A catalytic intramolecular nitrene insertion into a copper(i)-N-heterocyclic carbene bond yielding fused nitrogen heterocycles.
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.
Université Clermont Auvergne, CNRS, Sigma Clermont, ICCF, F-63000 Clermont-Ferrand, France. federico.cisnetti@uca.fr arnaud.gautier@uca.fr.
Kévin
K
Fauché
Université Clermont Auvergne, CNRS, Sigma Clermont, ICCF, F-63000 Clermont-Ferrand, France. federico.cisnetti@uca.fr arnaud.gautier@uca.fr.
Lionel
L
Nauton
Université Clermont Auvergne, CNRS, Sigma Clermont, ICCF, F-63000 Clermont-Ferrand, France. federico.cisnetti@uca.fr arnaud.gautier@uca.fr.
Laurent
L
Jouffret
Université Clermont Auvergne, CNRS, Sigma Clermont, ICCF, F-63000 Clermont-Ferrand, France. federico.cisnetti@uca.fr arnaud.gautier@uca.fr.
Federico
http://orcid.org/0000-0002-9446-4601
F
Cisnetti
Université Clermont Auvergne, CNRS, Sigma Clermont, ICCF, F-63000 Clermont-Ferrand, France. federico.cisnetti@uca.fr arnaud.gautier@uca.fr.
Arnaud
A
Gautier