Catalyst-controlled site-selective N-H and C3-arylation of carbazole via carbene transfer reactions

Sourav Sekhar Bera; Srishti Ballabh Bahukhandi; Claire Empel; Rene M Koenigs

doi:10.1039/d1cc01863a

Catalyst-controlled site-selective N-H and C3-arylation of carbazole via carbene transfer reactions

Chem Commun (Camb). 2021 Jun 22;57(50):6193-6196. doi: 10.1039/d1cc01863a.

Authors

Sourav Sekhar Bera¹, Srishti Ballabh Bahukhandi¹, Claire Empel¹, Rene M Koenigs¹

Affiliation

¹ RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, Aachen D-52074, Germany. rene.koenigs@rwth-aachen.de.

PMID: 34048520
DOI: 10.1039/d1cc01863a

Abstract

A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed. While Au(i)-NHC catalysts lead to selective C3-arylation, palladium acetate allows for selective N-H arylation, displaying complete site-selectivity each. To show the applicability of these arylation reactions, one-pot, two-fold diarylation reactions of carbazole were demonstrated.