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

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.

Automated summary

A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed, showing the potential for selective C3-arylation with Au(i)-NHC catalysts and selective N-H arylation with palladium acetate. The applicability of these arylation reactions was demonstrated through one-pot, two-fold diarylation reactions of carbazole.