3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes
Ren‐Xiao Liang, Ru‐Yi Chen, Chao Zhong, Jiawen Zhu, Zhong‐Yan Cao, Yi‐Xia Jia
Abstract
Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B2pin2) or PhMe2Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron- or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.
Topics & Concepts
ChemistryIntramolecular forceCatalysisArylSilaneIodideDominoIntermolecular forceOlefin fiberBoronAlkylCombinatorial chemistryMedicinal chemistryOrganic chemistryMoleculeOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods