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Domino cyclization/trifluoromethylation of 2-alkynylanilines using fluoroform-derived CuCF3: synthesis of 3-(trifluoromethyl)indoles

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Abstract

By employing easily accessible 2-alkynylanilines and the well-established fluoroform-derived CuCF3 reagent, a novel class of 3-(trifluoromethyl)indoles can be synthesized in good yields with no ambiguity of the CF3 position. The method utilizes a domino cyclization/trifluoromethylation strategy to construct the indole cores with the concomitant installation of the CF3 group. The ultimate source of CF3 is the low-cost industrial by-product fluoroform (CF3H).

Graphical abstract: Domino cyclization/trifluoromethylation of 2-alkynylanilines using fluoroform-derived CuCF3: synthesis of 3-(trifluoromethyl)indoles

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Publication details

The article was received on 22 Feb 2018, accepted on 14 Mar 2018 and first published on 20 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00191J
Citation: Org. Chem. Front., 2018, Advance Article
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    Domino cyclization/trifluoromethylation of 2-alkynylanilines using fluoroform-derived CuCF3: synthesis of 3-(trifluoromethyl)indoles

    Y. Ye, K. P. S. Cheung, L. He and G. C. Tsui, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00191J

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