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PhICl2 and Wet DMF: An Efficient System for Regioselective Chloroformyloxylation/α-Chlorination of Alkenes/α,β-Unsaturated Compounds

Le Liu, Daisy Zhang-Negrerie, Yunfei Du* and Kang Zhao*

*Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email: duyunfeiertju.edu.cn, kangzhaotju.edu.cn

L. Liu, D. Zhang-Negrerie, Y. Du, K. Zhao, Org. Lett., 2014, 16, 436-439.

DOI: 10.1021/ol403321n (free Supporting Information)



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Abstract

PhICl2 in wet DMF forms an efficient system for difunctionalization of various alkenes to provide either regioselective chloroformyloxylated products or α-chlorinated olefinic products, depending on the type of structure of the original unsaturated starting material. The mechanism of the reaction is proposed and discussed.

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Note

The reaction does not need to be protected under an inert atmosphere.

Yunfei Du, February 2, 2015


Key Words

chlorohydrins, chloroalkenes, iodobenzene dichloride


ID: J54-Y2014