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Issue 47, 2018
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Copper-mediated 1,2-bis(trifluoromethylation) of arynes

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We herein describe an unprecedented 1,2-bis(trifluoromethylation) of arynes with [CuCF3] in the presence of an oxidant DDQ. The method allows the rapid construction of a new class of 1,2-bis(trifluoromethyl)arenes in one-step from aryne precursors under mild conditions. Its synthetic utility has been demonstrated in the preparation of bis(trifluoromethylated) molecules with potential pharmaceutical and materials science applications. Mechanistic studies indicated the presence of an o-trifluoromethyl aryl radical intermediate via CF3 group transfer from [CuCF3] to the aryne.

Graphical abstract: Copper-mediated 1,2-bis(trifluoromethylation) of arynes

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The article was received on 22 Aug 2018, accepted on 20 Sep 2018 and first published on 21 Sep 2018

Article type: Edge Article
DOI: 10.1039/C8SC03754J
Citation: Chem. Sci., 2018,9, 8871-8875
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    Copper-mediated 1,2-bis(trifluoromethylation) of arynes

    X. Yang and G. C. Tsui, Chem. Sci., 2018, 9, 8871
    DOI: 10.1039/C8SC03754J

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