Benzyl Protection of Phenols under Neutral Conditions: Palladium-Catalyzed Benzylations of Phenols

Ryoichi Kuwano* and Hiroki Kusano

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

R. Kuwano, H. Kusano, Org. Lett., 2008, 10, 1795-1798.

DOI: 10.1021/ol800548t

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Abstract

A catalytic amount of Pd(η³-C₃H₅)Cp and DPEphos as ligand efficiently converted aryl benzyl carbonates into benzyl-protected phenols through a decarboxylative etherification. Alternatively, the nucleophilic substitution of benzyl methyl carbonates with phenols proceeded in the presence of the catalyst, yielding aryl benzyl ethers.

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proposed reaction pathway

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Key Words

benzyl ethers, aryl ethers

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ID: J54-Y2008-1240