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Ni‐Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX <sub>2</sub> **

Roshan K. Dhungana, Rishi R. Sapkota, Laura M. Wickham, Doleshwar Niroula, Bijay Shrestha, Ramesh Giri

2021Angewandte Chemie International Edition24 citationsDOIOpen Access PDF

Abstract

Abstract We report a Ni‐catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3‐triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate‐limiting single‐electron‐transfer process and is autocatalyzed by in‐situ‐generated ZnX 2 . The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX 2 .

Topics & Concepts

AutocatalysisKinetic energyCatalysisChemistryPhysicsQuantum mechanicsOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions
Ni‐Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX <sub>2</sub> ** | Litcius