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Issue 48, 2016
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Expeditious trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodoniums by [XCF3] (X = S, Se) anions

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Abstract

Trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodonium tosylates by [XCF3] (X = S, Se) ions was accomplished in 5–10 minutes at room temperature under a N2 atmosphere and provided a variety of alkynyl trifluoromethyl sulfides and selenides in good yields. Compared to the known methods, this approach has several advantages such as short reaction times and metal- and additive-free conditions without needing excess [Me4N][XCF3] reagents. Moreover, the less efficient reactions of (phenylethynyl)benziodoxol(on)e with [Me4N][XCF3] under the standard conditions demonstrate that acyclic alkynyl(phenyl)iodoniums are more powerful alkynyl sources in the conversion. This protocol allows for a fast and convenient access to numerous alkynyl trifluoromethyl sulfides and selenides.

Graphical abstract: Expeditious trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodoniums by [XCF3]− (X = S, Se) anions

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Publication details

The article was received on 27 Sep 2016, accepted on 17 Nov 2016 and first published on 17 Nov 2016


Article type: Paper
DOI: 10.1039/C6OB02107G
Org. Biomol. Chem., 2016,14, 11502-11509

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    Expeditious trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodoniums by [XCF3] (X = S, Se) anions

    W. Fang, T. Dong, J. Han, G. Zha and C. Zhang, Org. Biomol. Chem., 2016, 14, 11502
    DOI: 10.1039/C6OB02107G

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