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Nickel-Catalyzed Chemo- and Regioselective Arylcyanation of β,γ-Unsaturated Amides

Jinghui Hu, Qiang Du, Yao Zhao, Fei Zhang, Rizhi Chen, Jianrong Steve Zhou, Xiaojin Wu

2022Organic Letters19 citationsDOI

Abstract

A nickel-catalyzed intermolecular arylcyanation of 8-aminoquinolinyl β,γ-unsaturated amides is reported. The three-component reaction directly afforded diverse β-cyano γ-aryl amides with exclusive chemo- and regioselectivity. The synthetic practicality of this approach is further demonstrated through multigram scale reaction, expanded transformations of the nitrile product, late-stage modification of complex molecules, and direct drug synthesis.

Topics & Concepts

RegioselectivityChemistryCatalysisNitrileNickelIntermolecular forceCombinatorial chemistryArylMoleculeComponent (thermodynamics)Organic chemistryAlkylThermodynamicsPhysicsAdvanced Synthetic Organic ChemistryCatalytic C–H Functionalization MethodsCoordination Chemistry and Organometallics
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