Issue 6, 2015

Aerobic oxidation of cyclohexanones to phenols and aryl ethers over supported Pd catalysts

Abstract

Transformation of cyclohexanones to phenols and aryl ethers over supported Pd catalysts using molecular oxygen as the sole oxidant is developed. Several metal oxide supported Pd catalysts were used to activate the C–H bond in cyclohexanones to produce cyclohexenones and phenols through oxidation. Although the selectivity of cyclohexenones was difficult to control, phenols were obtained in excellent yield with a broad substrate scope. A novel catalytic system, using ZrO2 supported Pd(OH)2, was proposed for the synthesis of aryl ethers, and the products were obtained in moderate to excellent yields. Orthoesters, such as trimethyl orthoformate (TMOF), triethyl orthoformate (TEOF), and triisopropyl orthoformate (TIPOF), enabled nucleophilic addition and elimination after activation of cyclohexanones over a Pd catalyst to produce the corresponding aryl ethers. TIPOF was also used as the dehydrating reagent to promote the reaction of cyclohexanones with alcohols for the preparation of versatile aryl ethers.

Graphical abstract: Aerobic oxidation of cyclohexanones to phenols and aryl ethers over supported Pd catalysts

Supplementary files

Article information

Article type
Research Article
Submitted
31 dec 2014
Accepted
07 feb 2015
First published
12 feb 2015

Org. Chem. Front., 2015,2, 654-660

Author version available

Aerobic oxidation of cyclohexanones to phenols and aryl ethers over supported Pd catalysts

Z. Zhang, T. Hashiguchi, T. Ishida, A. Hamasaki, T. Honma, H. Ohashi, T. Yokoyama and M. Tokunaga, Org. Chem. Front., 2015, 2, 654 DOI: 10.1039/C4QO00354C

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