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Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons
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Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons
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Journal Article
Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons
2022
Overview
The transition metal-catalyzed hydrofunctionalization of alkenes offers an efficient solution for the rapid construction of complex functional molecules, and significant progress has been made during last decades. However, the hydrofunctionalization of internal alkenes remains a significant challenge due to low reactivity and the difficulties of controlling the regioselectivity. Here, we report the hydroarylation and hydroalkenylation of internal alkenes lacking a directing group with aryl and alkenyl boronic acids in the presence of a nickel catalyst, featuring a broad substrate scope and wide functional group tolerance under redox-neutral conditions. The key to achieving this reaction is the identification of a bulky 1-adamantyl
β
-diketone ligand, which is capable of overcoming the low reactivity of internal 1,2-disubstituted alkenes. Preliminary mechanistic studies unveiled that this reaction undergoes an Ar-Ni(II)-H initiated hydroarylation process, which is generated by the oxidative addition of alcoholic solvent with Ni(0) species and sequential transmetalation. In addition, the oxidative addition of the alcoholic solvent proves to be the turnover-limiting step.
The hydrocarbofunctionalization of alkenes represents one of the most efficient methods for generating complex products from simple starting materials. Here, the authors report a bulky β-diketone-ligand-enabled hydroarylation and hydroalkenylation of internal alkenes.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
