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
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 80°C. The reaction gave a variety of benzylic sulfones in high yields.
see article for more examples
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