Selective Oxidation of Benzylic Alcohols and TBDMS Ethers to Carbonyl Compounds with CrO₃-H₅IO₆

Suhong Zhang, Liang Xu, Mark L. Trudell*

*Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA, Email: mtrudelluno.edu

S. Zhang, L. Xu, M. L. Trudell, Synthesis, 2005, 1757-1760.

DOI: 10.1055/s-2005-869975

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Abstract

Benzyl alcohols and benzyl TBDMS ethers were efficiently oxidized to the corresponding carbonyl compounds in high yield with periodic acid catalyzed by CrO₃ at low temperature (-78 °C). The oxidation procedure was highly functional group tolerant and very selective for the TBDMS group over the TBDPS group.

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Key Words

oxidation, benzylic alcohols, aldehydes, ketones, chromium trioxide, periodic acid, BDMS ethers, Jones oxidation

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ID: J66-Y2005-1040