Electrophilic alkynylation: the dark side of acetylene chemistry

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=C bond alkynylation has also been reported. Finally, sulfonyl acetylenes are efficient for alkyne transfer on carbon-centered radicals.


Published in:
Chemical Society Reviews, 41, 4165-4179
Year:
2012
Publisher:
Royal Society of Chemistry
ISSN:
0306-0012
Keywords:
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 Record created 2012-06-01, last modified 2018-03-17

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