Mild Debenzylation of Aryl Benzyl Ether with BCl₃ in the Presence of Pentamethylbenzene as a Non-Lewis-Basic Cation Scavenger

Kentaro Okano, Kei-ichiro Okuyama, Tohru Fukuyama, Hidetoshi Tokuyama*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan, Email: tokuyamamail.pharm.tohoku.ac.jp

K. Okano, K.-i. Okuyama, T. Fukuyama, H. Tokuyama, Synlett, 2008, 1977-1980.

DOI: 10.1055/s-2008-1077980

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Abstract

A chemoselective debenzylation of aryl benzyl ethers proceeds at low temperature with a combination of BCl₃ and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

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Key Words

protecting groups, total synthesis, phenols, debenzylation, aryl benzyl ethers

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ID: J60-Y2008-2150