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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… Click to show full abstract
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.
Journal Title: Organic letters
Year Published: 2022
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