Organic Chemistry Portal



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:,

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

DOI: 10.1021/ol403321n (free Supporting Information)

see article for more reactions


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.

see article for more examples


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