Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives
Xiaoyu Zhang, Chao Ning, Yong-Jie Long, Yin Wei, Min Shi
Abstract
A visible-light-mediated decarboxylative tandem carbocyclization of acrylamide-tethered alkylidenecyclopropanes with phenyliodine(III) diacetate and various aliphatic acids has been reported in this paper. An alkyl radical in situ generated from phenyliodine(III) dicarboxylates upon visible-light irradiation catalyzed by fac-Ir(ppy)3 adds to the less hindered central carbon of alkylidenecyclopropane to initiate the tandem annulation, generating tetracyclic benzazepine derivatives in moderate to good yields with broad substrate scope under mild conditions.
Topics & Concepts
ChemistryTandemBenzazepineAnnulationAcrylamideAlkylSubstrate (aquarium)Combinatorial chemistryMedicinal chemistryPhotochemistryStereochemistryOrganic chemistryCatalysisPolymerGeologyOceanographyMaterials scienceComposite materialCopolymerCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods