Suzuki coupling catalyzed by chloro({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethylphenyl}methyl-κC)palladium(II)

Add time:07/16/2019    Source:sciencedirect.com

The title compound was evaluated as catalyst for Suzuki coupling of aryl halides (X = I, Br) with phenylboronic acid at room temperature. The rates of the reactions increase with increasing Hammet sigma constant of m-substituents on the arylhalide. The presence of ortho groups on the arylhalides had the effect of lowering the reaction rates. Density functional theory study of the mechanism for the formation of a Pd(0) complex from the title molecule was performed. Reductive elimination of chloride and the η4-BCCC moiety was endergonic and ruled out as a likely pathway. Instead, conversion of the title molecule to phenyl({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethylphenyl}methyl-κC)palladium(II) complex is thermodynamically favored and predicted to further react with the solvent and the Suzuki coupling reagents to undergo reductive elimination of diphenyl to form a reactive Pd(0) complex.

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