Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions

Zhi-Jiang Jiang, Zhen-Hua Li*, Jing-Bo Yu and Wei-Ke Su*

*Zhejiang University of Technology, Hangzhou 310014, P. R. China, Email: lizhenhuazjut.edu.cn, pharmlabzjut.edu.cn

Z.-J. Jiang, Z.-H. Li, J.-B. Yu, W.-K. Su, J. Org. Chem., 2016, 81, 10049-10055.

DOI: 10.1021/acs.joc.6b01938

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Abstract

In a mechanical Suzuki-Miyaura reaction of aryl chlorides, an unexpected improvement of yield is observed using alcohols as additives, which is explained by in situ formed alkoxides and their participation in oxidative addition. Liquid-assisted grinding with a Pd(OAc)₂/PCy₃/MeOH system provides desired products in very good yields.

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Key Words

Suzuki coupling, biaryls, mechanochemistry

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ID: J42-Y2016