Suzuki-Miyaura Cross-Coupling of Benzylic Carbonates with Arylboronic Acids

Ryoichi Kuwano* and Masashi Yokogi

*Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Email: rkuwasccmbox.nc.kyushu-u.ac.jp

R. Kuwano, M. Yokogi, Org. Lett., 2005, 7, 945-947.

DOI: 10.1021/ol050078q

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Abstract

The palladium-catalyzed cross-coupling of various benzylic carbonates with arylboronic acids gave the corresponding diarylmethanes in high yields. The catalyst is generated in situ from [Pd(η³-C₃H₅)Cl]₂ and 1,5-bis(diphenylphosphino)pentane (dpppe).

see article for more examples

proposed mechanism

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Transformation of Carbonates into Sulfones at the Benzylic Position via Palladium-Catalyzed Benzylic Substitution

R. Kuwano, Y. Kondo, T. Shirahama, Org. Lett., 2005, 7, 2973-2975.

Palladium-Catalyzed Nucleophilic Benzylic Substitutions of Benzylic Esters

R. Kuwano, Y. Kondo, Y. Matuyama, J. Am. Chem. Soc., 2003, 125, 12104-12105.

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Key Words

Suzuki-Coupling, Benzylation

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ID: J54-Y2005-250