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syn-Fluoro- and -Oxy-trifluoromethylation of Arylacetylenes
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    syn-Fluoro- and -Oxy-trifluoromethylation of Arylacetylenes
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    Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, China
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6372–6375
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    https://doi.org/10.1021/acs.orglett.7b03229
    Published November 20, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    One-step concurrent fluoro-trifluoromethylation across the triple bond of arylacetylenes in a syn mode is enabled by the collaboration of (phen)CuIII(CF3)3 and CsF that produces chemo-, regio-, and stereoselectively (Z)-α-fluoro-β-CF3 styrenes. This method can be extended to achieve syn-oxy-trifluoromethylation and syn-aryl-trifluoromethylation of alkynes using phenoxides, alkoxides, or phenylboronic acid in place of CsF. It opens up new opportunities for preparing various functionalized trifluoromethylated Z-alkenes and demonstrates the potential of Cu(III)–CF3 complexes in organic synthesis.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b03229.

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6372–6375
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b03229
    Published November 20, 2017
    Copyright © 2017 American Chemical Society

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