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Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes.

Marcos G Suero, Elliott D Bayle, Beatrice S L Collins, Matthew J Gaunt

Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.

Journal of the American Chemical Society 2013 Apr 10


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  • alkenes (4)
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    Copper catalysts enable the electrophilic carbofunctionalization of alkynes with vinyl- and diaryliodonium triflates. The new process forms highly substituted alkenyl triflates from a range of alkynes via a pathway that is opposite to classical carbometalation. The alkenyl triflate products can be elaborated through cross-coupling reactions to generate synthetically useful tetrasubstituted alkenes.

    Citation

    Marcos G Suero, Elliott D Bayle, Beatrice S L Collins, Matthew J Gaunt. Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes. Journal of the American Chemical Society. 2013 Apr 10;135(14):5332-5

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    PMID: 23521626

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