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Pd-Catalyzed Enantioselective Three-Component Carboamination of 1,3-Cyclohexadiene

Jinrong Wang, Bing Xu, Yibo Wang, Guangzhen Xia, Zhan‐Ming Zhang, Junliang Zhang

2024Journal of the American Chemical Society25 citationsDOI

Abstract

Asymmetric Pd-catalyzed three-component carboamination reactions of dienes to construct chiral cyclohexenylamines, which are of great importance in many fields of chemistry, have remained largely unexplored. Here, we demonstrate a highly enantio- and regioselective Pd/ Ming-Phos -catalyzed carboamination reactions of 1,3-cyclohexadiene with readily available aryl iodides and anilines for facile access to diverse valuable chiral cyclohexenylamines. The process shows excellent functional group tolerance, easy scalability, and mild conditions. Moreover, mechanistic studies suggest that this reaction has a first-order dependence on the concentration of the palladium catalyst and aniline.

Topics & Concepts

ChemistryEnantioselective synthesisCatalysisComponent (thermodynamics)Organic chemistryThermodynamicsPhysicsAsymmetric Hydrogenation and CatalysisCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods