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Tetrabutylammonium 2-Pyridyltriolborate Salts for Suzuki-Miyaura Cross-Coupling Reactions with Aryl Chlorides

Shohei Sakashita, Miho Takizawa, Juugaku Sugai, Hajime Ito and Yasunori Yamamoto*

*Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan, Email:

S. Sakashita, M. Takizawa, J. Sugai, H. Ito, Y. Yamamoto, Org. Lett., 2013, 15, 4308-4311.

DOI: 10.1021/ol402268g (free Supporting Information)

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A Suzuki-Miyaura cross-coupling of tetrabutylammonium 2-pyridyltriolborate salts with various aryl and heteroaryl chlorides produces the corresponding desired coupling products with good to excellent yields in the presence of catalytic amounts of PdCl2dcpp and CuI/MeNHCH2CH2OH in anhydrous DMF without bases. Tetrabutylammonium 2-pyridyltriolborate salts are more reactive than the corresponding lithium salts.

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Key Words

Pyridines, Heterobiaryls, Suzuki Coupling

ID: J54-Y2013