Nickel-Catalyzed Arylcarbamoylation of Alkenes of <i>N</i>-(<i>o</i>-Iodoaryl)acrylamides with Nitroarenes via Reductive Aminocarbonylation: Facile Synthesis of Carbamoyl-Substituted Oxindoles
Chaozhihui Cheng, Jiannan Xiang, Yanping Zhu, Zhihong Peng, Jin‐Heng Li
Abstract
Nickel-catalyzed arylcarbamoylation reactions of alkenes of N-(o-haloaryl)acrylamides with CO and nitroarenes via reductive aminocarbonylation to produce carbamoyl-substituted oxindoles with an all-carbon quaternary stereogenic center are presented. Starting with N-(o-haloaryl)acrylamides, simple CO, and inexpensive nitroarenes and using a Ni catalyst, a dinitrogen-based ligand, a Zn reductant, a TMSCl additive, and a base system, this protocol enables the synthesis of various carbamoyl-substituted oxindoles and allows the efficient late-stage derivatization of valuable molecules.
Topics & Concepts
ChemistryStereocenterCatalysisNickelCombinatorial chemistryLigand (biochemistry)DerivatizationMedicinal chemistryOrganic chemistryEnantioselective synthesisBiochemistryReceptorHigh-performance liquid chromatographyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques