Cascade C–H Activation and Defluorinative Annulation of 2-Arylbenzimidazoles with α-Trifluoromethyl-α-diazoketones: Modular Assembly of 6-Fluorobenzimidazo[2,1-<i>a</i>]isoquinolines
Zhongkang Dong, Hengzhi Zhang, Baiquan Wang, Bin Li
Abstract
A novel Ru-catalyzed redox-neutral [4+2] cyclization of 2-arylbenzimidazoles with α-trifluoromethyl-α-diazoketones has been achieved through sequential C–H activation and defluorinative annulation. This synthetic protocol unlocks modular and expeditious access to 6-fluorobenzimidazo[2,1- a ]isoquinolines with high efficiency and excellent functional group compatibility. The resultant monofluorinated heterocyclic products can readily diversified by various nucleophiles.
Topics & Concepts
AnnulationChemistryTrifluoromethylNucleophileCombinatorial chemistryModular designRedoxStereochemistryCatalysisOrganic chemistryAlkylOperating systemComputer scienceFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods