Rhodium-Catalyzed Atroposelective C-H/C-H Cross-Coupling Reaction between 1-Aryl Isoquinoline Derivatives and Indolizines

A rhodium-catalyzed asymmetric oxidative C-H/C-H cross-coupling reaction between 1-aryl isoquinolines and indolizines is disclosed. With a matched pair of SCpRh complex and chiral carboxylic acid, enantioselective two-fold C-H/C-H cross-coupling reactions between 1-aryl isoquinolines and indolizines provide a variety of axially chiral bi(hetero)aryls in excellent yields and enantioselectivity (up to 96% yield and 98% ee). Mechanistic studies suggest that both C-H cleavages are likely reversible.

Automated summary

A rhodium-catalyzed asymmetric oxidative C-H/C-H cross-coupling reaction has been developed for the synthesis of axially chiral bi(hetero)aryls. The reaction showed high yields and enantioselectivity, and mechanistic studies suggested the reversibility of C-H cleavage.