Palladium-Catalyzed Carbene Migratory Insertion/Carbonylation Cascade Reaction: Synthesis of 2-Indolones with a C3 All-Carbon Quaternary Center
Ming Cheng, Xiaoyan Huang, Fang Yang, Dongmei Zhao, Ke‐Gong Ji, Zi‐Sheng Chen
Abstract
An attractive palladium-catalyzed three-component reaction of ortho-amino aryl diazo esters, allyl carboxylates, and carbon monoxide (CO) has been developed. This catalytic system rendered domino carbene migratory insertion and carbonylation. Remarkably, 2-indolones 3 with a C3 all-carbon quaternary center can be selectively obtained in good to excellent yields via one-pot synthesis, in which two different C–C bonds and one C–N bond were formed in a straightforward manner.
Topics & Concepts
ChemistryCarbenePalladiumMigratory insertionCatalysisCarbonylationCascade reactionDiazoCarbon monoxideArylQuaternary carbonInsertion reactionDominoMedicinal chemistryCombinatorial chemistryPhotochemistryOrganic chemistryEnantioselective synthesisAlkylCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions