Highly Selective Synthesis of 2-tert-Butoxy-1-Arylethanones via Copper(I)-Catalyzed Oxidation/tert-Butoxylation of Aryl Olefins with TBHP

Jiantao Zhang, Duoduo Xiao*, Hua Tan and Weibing Liu*

*College of Chemistry, Guangdong University of Petrochemical Technology, Guandu Road, Maoming 525000, People’s Republic of China, Email: dd.xiaogdupt.edu.cn, lwb409gdupt.edu.cn

J. Zhang, D. Xiao, H. Tan, W. Liu, J. Org. Chem., 2020, 85, 3929-3935.

DOI: 10.1021/acs.joc.9b03156

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Abstract

A practical and environmentally friendly oxidation of aryl olefins to arylethanone derivatives by using a Cu(I) catalyst and tert-butyl hydroperoxide (TBHP) provides 2-tert-butoxy-1-arylethanones in good yields under mild conditions with high selectivity. In this method, TBHP acts not only as an oxidant but also as the tert-butoxy and carbonyl oxygen sources.

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Key Words

α-hydroxy ketones, tert-butyl ethers, TBHP

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ID: J42-Y2020