Volume 241, 2023

The impact of the physical state and the reaction phase in the direct mechanocatalytic Suzuki–Miyaura coupling reaction

Abstract

The direct mechanocatalytic Suzuki–Miyaura coupling reaction, utilizing palladium milling balls as active catalysts, was investigated regarding the physical state of the reagents and the reaction phase. The substitution patterns and functional groups of different aryl iodides were varied and different boronic acid derivates were utilized to achieve a wide range of substrate combinations. In the neat grinding experiments, liquid aryl iodides were more reactive than solid ones and a steric influence of the substituents, especially pronounced in ortho compounds, was observed. In order to overcome the general low reactivity of the solid phase, several liquid-assisted grinding experiments were conducted and the influence of substrate solubility and catalyst wettability analyzed. Among all LAG additives, EtOH showed the greatest impact on the reactivity, as it converts boronic acid derivatives into liquid and reactive esters under mechanochemical conditions, significantly speeding up the reaction.

Graphical abstract: The impact of the physical state and the reaction phase in the direct mechanocatalytic Suzuki–Miyaura coupling reaction

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
12 Mey 2022
Accepted
22 Jun 2022
First published
22 Jun 2022

Faraday Discuss., 2023,241, 206-216

The impact of the physical state and the reaction phase in the direct mechanocatalytic Suzuki–Miyaura coupling reaction

K. Yoo, S. Fabig, S. Grätz and L. Borchardt, Faraday Discuss., 2023, 241, 206 DOI: 10.1039/D2FD00100D

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