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Issue 38, 2018
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Synthesis of difluoromethylated enynes by the reaction of α-(trifluoromethyl)styrenes with terminal alkynes

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Abstract

A novel and efficient method for the synthesis of difluoromethylated enynes by the reaction of α-(trifluoromethyl)styrenes with terminal alkynes with the assistance of NaOtBu was described. The mechanism of the reaction might involve the SN2′ reaction of α-(trifluoromethyl)styrenes and a subsequent 1,3-H shift. Isomerization (E → Z) of 1-difluoromethyl-1,3-enynes in the presence of ZrCl4 was also developed.

Graphical abstract: Synthesis of difluoromethylated enynes by the reaction of α-(trifluoromethyl)styrenes with terminal alkynes

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Publication details

The article was received on 29 Aug 2018, accepted on 11 Sep 2018 and first published on 11 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02117A
Citation: Org. Biomol. Chem., 2018,16, 6909-6917
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    Synthesis of difluoromethylated enynes by the reaction of α-(trifluoromethyl)styrenes with terminal alkynes

    M. Wu, X. Zhao, Y. Liu and S. Cao, Org. Biomol. Chem., 2018, 16, 6909
    DOI: 10.1039/C8OB02117A

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