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: songliyanfafu.edu.cn, linranfafu.edu.cn, rtongust.hk

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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Abstract

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

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ID: J42-Y2023