Palladium-Catalyzed Tandem Nucleophilic Addition/C–H Functionalization of Anilines and Bromoalkynes for the Synthesis of 2-Phenylindoles
Caijin Zeng, Songjia Fang, Shuqi Guo, Huanfeng Jiang, Shaorong Yang, Wanqing Wu
Abstract
A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis of 2-phenylindoles has been described. This approach features excellent regio- and stereoselectivities and good functional group tolerance. Preliminary mechanistic studies indicate that anilines undergo anti -nucleophilic addition to bromoalkynes to generate ( Z )- N -(2-bromo-1-phenylvinyl) anilines, followed by sequential C–H functionalization to deliver different substituted 2-phenylindoles. This method provides potential applications for the construction of various biologically active compounds.
Topics & Concepts
ChemistryPalladiumSurface modificationNucleophileTandemAnnulationCatalysisFunctional groupCombinatorial chemistryNucleophilic additionOrganic chemistryPolymerPhysical chemistryMaterials scienceComposite materialCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques