An Efficient Approach for 3,3-Disubstituted Oxindoles Synthesis: Aryl Iodine Catalyzed Intramolecular C–N Bond Oxidative Cross-Coupling
Yang Wang, Mo Yang, Yuanyuan Sun, Zheng‐Guang Wu, Hong Dai, Shuhua Li
Abstract
Herein, we report the first intramolecular C-N bond formation of phenylpropanamide derivatives via organocatalytic oxidative reactions, affording 3,3-disubstituted oxindole derivatives with up to 99% yield. The high efficiency of this reaction is exemplified by the transition metal-free mild conditions and the ability to perform the reaction on a gram scale. Meanwhile, the DFT calculation of the catalytic oxidative transformation pathway has also been studied.
Topics & Concepts
ChemistryIntramolecular forceOxindoleCatalysisYield (engineering)ArylOxidative phosphorylationIodineCombinatorial chemistryOxidative coupling of methaneMedicinal chemistryOrganic chemistryAlkylMetallurgyBiochemistryMaterials scienceCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsAlkaloids: synthesis and pharmacology