Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3.2H2O selectively promoted an intramolecular radical C-H/C-H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while an intramolecular radical C-H/N-H dehydrogenative coupling reaction could proceed via electrochemistry to deliver isoindolo[2,1-a]indoles. Plausible mechanisms of the chemodivergent reactions were proposed.

Automated summary

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials has been achieved. Mn(OAc)3.2H2O selectively promotes different reactions leading to the formation of two distinct products.