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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:,

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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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

Key Words

dihydroxylation, peroxides, TBHP

ID: J42-Y2021