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Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols

Feng-Qing Huang, Jian Xie, Jian-Guo Sun, Yue-Wei Wang, Xin Dong, Lian-Wen Qi* and Bo Zhang*

*State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China, Email: zb3981444cpu.edu.cn, Qilwcpu.edu.cn

F.-Q. Huang, J. Xie, J.-Guo Sun, Y.-W. Wang, X. Dong, L-W. Qi, B. Zhang, Org. Lett., 2016, 18, 684-687.

DOI: 10.1021/acs.orglett.5b03649 (free Supporting Information)


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Abstract

A silver-catalyzed ring-opening chlorination of cycloalkanols enables a regioselective, efficient, and pratical approach to carbonyl-containing alkyl chlorides with good yields under mild conditions. The chlorinated products are readily transformed into other useful synthetic intermediates and drugs.

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Key Words

chlorination, tert-butyl hypochlorite


ID: J54-Y2016