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Nickel-Catalyzed Chemo- and Regioselective Benzylarylation of Unactivated Alkenes with <i>o</i>-Bromobenzyl Chlorides

Hailong Wang, Haichao Huang, Chao Gong, Yong Diao, Jianmei Chen, Si‐Hai Wu, Lianhui Wang

2021Organic Letters11 citationsDOI

Abstract

Chemo- and regioselectively nickel-catalyzed reductive benzylarylation of unactivated alkenes with o-bromobenzyl chlorides is disclosed herein, in which electrophiles participate through a single-component double-site approach. Moreover, its utility is underscored by the concise synthesis of bioactive Indane compounds and postreaction functionalizations leading to structurally diverse scaffolds. Preliminary mechanistic investigations suggest a radical chain reaction mechanism.

Topics & Concepts

ChemistryIndaneRegioselectivityCatalysisElectrophileCombinatorial chemistryNickelReductive eliminationComponent (thermodynamics)Organic chemistryThermodynamicsPhysicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Nickel-Catalyzed Chemo- and Regioselective Benzylarylation of Unactivated Alkenes with <i>o</i>-Bromobenzyl Chlorides | Litcius