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Nickel-catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes

Wei‐Song Zhang, Ding‐Wei Ji, Ying Li, Xiang‐Xin Zhang, Yong‐Kang Mei, Bingzhi Chen, Qing‐An Chen

2023Nature Communications28 citationsDOIOpen Access PDF

Abstract

Abstract Developing efficient strategies to realize divergent arylation of dienes has been a long-standing synthetic challenge. Herein, a nickel catalyzed divergent Mizoroki–Heck reaction of 1,3-dienes has been demonstrated through the regulation of ligands and additives. In the presence of Mn/NEt 3 , the Mizoroki–Heck reaction of dienes delivers linear products under Ni(dppe)Cl 2 catalysis in high regio- and stereoselectivities. With the help of catalytic amount of organoboron and NaF, the use of bulky ligand IPr diverts the selectivity from linear products to branched products. Highly aryl-substituted compounds can be transformed from dispersive Mizoroki–Heck products programmatically. Preliminary experimental studies are carried out to elucidate the role of additives.

Topics & Concepts

CatalysisNickelChemistryHeck reactionArylLigand (biochemistry)Combinatorial chemistryOrganic chemistryPalladiumBiochemistryReceptorAlkylCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis
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