Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

Xiaofang Gao, Jiani Lin, Li Zhang, Xinyao Lou, Guanghui Guo, Na Peng, Huan Xu* and Yi Liu*

*College of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, P. R. China, Email: xuhuanwust.edu.cn, yiliuchemwhu.edu.cn

X. Gao, J. Lin, L. Zhang, X. Luo, G. Guo, N. Peng, H. Xu, Y. Liu, J. Org. Chem., 2021, 86, 15469-15480.

DOI: 10.1021/acs.joc.1c01968

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Abstract

Iodine catalyzes an environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols in water as solvent with tert-butylhydroperoxide (TBHP) as the oxidant. The protocol is efficient, sustainable, and operationally simple. In addition, bisperoxides could be obtained in good yields with Na₂CO₃ as additive and propylene carbonate as solvent.

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proposed mechanism

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Key Words

dihydroxylation, peroxides, TBHP

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ID: J42-Y2021