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Two Green Protocols for Halogenative Semipinacol Rearrangement

Liyan Song*, Yiqin Zhou, Hanbin Liang, Hongzuo Li, Yunrong Lai, Hongliang Yao, Ran Lin* and Rongbiao Tong*

*Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002; HKUST, Clearwater Bay, Kowloon, Hong Kong 999077, China, Email:,,

L. Song, Y. Zhou, H. Liang, H. Li, Y. Lai, H. Yao, R. Lin, R. Tong, J. Org. Chem., 2023, 88, 504-512.

DOI: 10.1021/acs.joc.2c02496

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A convenient, safe, and green protocol, that uses oxone/halide and Fenton bromide, achieves a halogenative semipinacol rearrangement at room temperature. The key feature of this method is the green in situ generation of reactive halogenating species from oxidation of halide with oxone or H2O2, which produces a nontoxic byproduct (potassium sulfate or water).

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Key Words

cyclopentanones, bromination, iodination, hydrogen peroxide, oxone, pinacol rearrangement

ID: J42-Y2023