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Issue 11, 2012
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Electrophilic alkynylation: the dark side of acetylene chemistry

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Abstract

In addition to the well-established nucleophilic alkynylation, the use of electrophilic alkynes can expand tremendously the scope of acetylene transfer reactions. The use of metal catalysis has recently led to a rebirth of this research area. Halogenoalkynes, hypervalent alkynyliodoniums, acetylene sulfones and in situ oxidized terminal acetylenes are the most often used reagents for electrophilic alkynylation. Heteroatoms such as N, O, S and P can be now efficiently alkynylated. For C–C bond formation, electrophilic acetylenes can be coupled with different organometallic reagents. Recently, the first breakthrough in direct C–H and C[double bond, length as m-dash]C bond alkynylation has also been reported. Finally, sulfonyl acetylenes are efficient for alkyne transfer on carbon-centered radicals.

Graphical abstract: Electrophilic alkynylation: the dark side of acetylene chemistry

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Publication details

The article was received on 03 Feb 2012 and first published on 18 Apr 2012


Article type: Tutorial Review
DOI: 10.1039/C2CS35034C
Citation: Chem. Soc. Rev., 2012,41, 4165-4179
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    Electrophilic alkynylation: the dark side of acetylene chemistry

    J. P. Brand and J. Waser, Chem. Soc. Rev., 2012, 41, 4165
    DOI: 10.1039/C2CS35034C

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