Rhodium-Catalyzed Atroposelective C-H Arylation of(Hetero)Arenes Using Carbene Precursors as Arylating Reagents

Rhodium(III)-catalyzed C-H activation-based arylation of sterically hindered (hetero)arenes has been realized usingdiazo compounds and triazoles as arylating reagents for atroposelective synthesis of two classes of biaryls. The coupling of 3-substituted indoles andN-sulfonyltriazoles afforded indoles with a C(2)-C chiral axis, while the arylation of 1-naphthylthioetherwithortho-quinone diazide afforded chiral binaphthyls. These coupling systems proceeded under mild conditions via C-H activationand carbene insertion despite the steric hindrance of both the arenes and the carbene precursors

Automated summary

In this study, the Rhodium(III)-catalyzed C-H activation-based arylation of sterically hindered (hetero)arenes was achieved using diazo compounds and triazoles as arylating reagents, enabling the atroposelective synthesis of two classes of biaryls under mild conditions.