Rhodium-Catalyzed Atroposelective C–H Arylation of (Hetero)Arenes Using Carbene Precursors as Arylating Reagents
Organic Letters(2022)
摘要
Rhodium(III)-catalyzed C–H activation-based arylation of sterically hindered (hetero)arenes has been realized using diazo compounds and triazoles as arylating reagents for atroposelective synthesis of two classes of biaryls. The coupling of 3-substituted indoles and N-sulfonyltriazoles afforded indoles with a C(2)–C chiral axis, while the arylation of 1-naphthylthioether with ortho-quinone diazide afforded chiral binaphthyls. These coupling systems proceeded under mild conditions via C–H activation and carbene insertion despite the steric hindrance of both the arenes and the carbene precursors.
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