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Iodosobenzene-Mediated α-Acyloxylation of 1,3-Dicarbonyl Compounds with Carboxylic Acids and Insight into the Reaction Mechanism

Chitturi Bhujanga Rao, Jingwen Yuan, Qian Zhang, Rui Zhang*, Ning Zhang, Jianyong Fang and Dewen Dong*

*Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China, Email: arielciac.ac.cn, dwdongciac.ac.cn

C. B. Rao, J. Yuan, Q. Zhang, R. Zhang, N. Zhang, J. Fang, D. Dong, J. Org. Chem., 2018, 83, 2904-2911.

DOI: 10.1021/acs.joc.8b00114 (free Supporting Information)


Abstract

A highly efficient direct α-acyloxylation of 1,3-dicarbonyl compounds with carboxylic acids is mediated by iodosobenzene. The reaction of various 1,3-dicarbonyl compounds with carboxylic acids provides the corresponding α-acyloxylated products in good to excellent yields under mild reaction conditions. The loading sequence of reactants and oxidant is crucial for the generation of the active species.

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Key Words

hydroxylation, iodosobenzene


ID: J42-Y2018