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

Ryoichi Kuwano,* Yutaka Kondo and Tsuyoshi Shirahama

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

DOI: 10.1021/ol0509787 (free Supporting Information)


Abstract

A palladium complex generated in situ from [Pd(η3-C3H5)Cl]2 and DPEphos [bis(2-diphenylphosphinophenyl)ether] catalyzed the nucleophilic substitution of benzylic carbonates with sodium arenesulfinates in DMSO at 80C. The reaction gave a variety of benzylic sulfones in high yields.

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

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

Palladium-Catalyzed Nucleophilic Benzylic Substitutions of Benzylic Esters

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


Key Words

Sulfones, Benzylic Substitution, Palladium Catalysis


ID: J54-Y2005-810