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

Yun ZouPeiyuan WangLingheng KongXingwei Li
Published in: Organic letters (2022)
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.
Keyphrases
  • room temperature
  • ionic liquid
  • capillary electrophoresis
  • molecular docking
  • mass spectrometry