SO₂F₂-Mediated Epoxidation of Olefins with Hydrogen Peroxide

Chengmei Ai, Fuyuan Zhu, Yanmei Wang, Zhaohua Yan* and Sen Lin*

*College of Chemistry, Nanchang University, Nanchang 330031, P. R. China, Email: yanzhncu.edu.cn, senlinncu.edu.cn

C. Ai, F. Zhu, Y. Wang, Z. Yan, S. Lin, J. Org. Chem., 2019, 84, 11928-11934.

DOI: 10.1021/acs.joc.9b01784

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Abstract

Bubbling SO₂F₂ gas into a solution of olefin, 30% aqueous hydrogen peroxide, and 2 M aqueous potassium carbonate in 1,4-dioxane at room temperature for 1 h provides the corresponding epoxides in good to excellent yields. This inexpensive, mild, and highly efficient epoxidizing system is suitable to a variety of olefinic substrates including electron-rich and electron-deficient ones.

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Key Words

epoxidation, hydrogen peroxide

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ID: J42-Y2019