Cu-Catalyzed Oxidative Dual Arylation of Active Alkenes: Preparation of Cyanoarylated Oxindoles through Denitrogenation of 3-Aminoindazoles
Qiaolin Wang, Quan Zhou, Jia Liao, Zan Chen, Biquan Xiong, Guo‐Jun Deng, Kewen Tang, Yu Liu
Abstract
A novel and mild Cu-catalyzed oxidative dual arylation of carbon-carbon double bonds in acrylamides with 3-aminoindazoles is proposed for the synthesis of cyanoarylated oxindoles. Notably, 3-aminoindazoles are employed as efficient arylating agents via the cleavage of two C-N bonds. This oxidative dual arylation of active alkenes involves a radical process and undergoes a sequence of 3-aminoindazole oxidation, two-C-N-bond cleavage, cyanoaryl radical addition, and intramolecular cyclization.
Topics & Concepts
ChemistryIntramolecular forceCatalysisOxidative phosphorylationBond cleavageCleavage (geology)Combinatorial chemistryMedicinal chemistryOrganic chemistryEngineeringBiochemistryGeotechnical engineeringFracture (geology)Catalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions