Chemodivergent Synthesis of Indeno[1,2-<i>b</i>]indoles and Isoindolo[2,1-<i>a</i>]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling
Piao Lu, Weihui Zhuang, Leipeng Lu, Anyi Liu, Yixi Chen, Chenmeng Wu, Xiaofeng Zhang, Qiufeng Huang
Abstract
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.
Topics & Concepts
Intramolecular forceElectrochemistryChemistryCoupling (piping)Combinatorial chemistryMedicinal chemistryStereochemistryMaterials sciencePhysical chemistryMetallurgyElectrodeCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions