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Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides

Xiaojun Zeng, Zhichao Lu, Shiwen Liu, Gerald B. Hammond* and Bo Xu*

*University of Louisville, Louisville, Kentucky 40292, United States; Donghua University, 2999 North Renmin Lu, Shanghai 201620, China, Email: gb.hammondlouisville.edu, bo.xudhu.edu.cn

X. Zeng, Z. Lu, S. Liu, G. B. Hammond, B. Xu, J. Org. Chem., 2017, 82, 13179-13187.

DOI: 10.1021/acs.joc.7b02257 (free Supporting Information)


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Abstract

The use of easy to handle DMPU/HX (X = Br or Cl) reagents enables an atom-economical and metal-free method for the regio- and stereo-selective hydrohalogenation of ynones and ynamides under mild conditions. The reaction tolerates a wide range of functional groups.

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proposed mechanism



Key Words

vinyl chlorides, vinyl bromides


ID: J42-Y2017