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

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Ryoichi Kuwano and Hiroki Kusano

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

Org. Lett., 2008, 10 (10), pp 1979–1982

DOI: 10.1021/ol800548t

Publication Date (Web): April 11, 2008

Abstract

Benzyl protection of phenols under neutral conditions was achieved by using a Pd(η³-C₃H₅)Cp–DPEphos catalyst. The palladium catalyst efficiently converted aryl benzyl carbonates into benzyl-protected phenols through the 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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History

Published In Issue May 15, 2008
Article ASAPApril 11, 2008
Received: March 10, 2008
Accepted: March 26, 2008

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Letter

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