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Palladium-Catalyzed Nucleophilic Benzylic Substitutions of Benzylic Esters

Ryoichi Kuwano,* Yutaka Kondo and Yosuke Matsuyama

*Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Email:

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

DOI: 10.1021/ja037735z


A palladium complex generated in situ from [Pd(η3-C3H5)(cod)]BF4 and DPPF is a good catalyst for benzylations of malonates with a wide range of benzyl methyl carbonates. The DPEphos ligand is superior to DPPF in the case of palladium-catalyzed benzylic amination of benzylic esters.

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.

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.

Key Words

Active Methylenes, Benzylic Amines

ID: J48-Y2003-1620