Catalytic nitrile-alkyne cross-metathesis

Andrea M. Geyer, Robyn L. Gdula, Eric Wiedner, Marc J A Johnson

Research output: Contribution to journalArticle

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Abstract

The first catalytic cross-metathesis reaction of an alkyne with a nitrile is described. The nitride complex NW(OC(CF3)2CH3)3(DME) undergoes reversible triple-bond metathesis reactions with alkynes (RCCR; R = Et, 4-C6H4OMe), forming the alkylidyne complexes RCW(OC(CF3)2CH3)3(DME) (R = Et, 4-C6H4OMe) along with the corresponding nitrile RCN. This has been exploited to effect catalytic cross-metathesis of nitriles with alkynes, in which the organic CR fragments of two nitriles are coupled to yield an alkyne. A simple "sacrificial" alkyne (3-hexyne) acts as the N-atom acceptor, forming two equivalents of nitrile byproduct (propionitrile).

Original languageEnglish
Pages (from-to)3800-3801
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number13
DOIs
Publication statusPublished - Apr 4 2007

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Nitriles
Alkynes
Nitrides
Byproducts
Atoms
Cross Reactions

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Catalytic nitrile-alkyne cross-metathesis. / Geyer, Andrea M.; Gdula, Robyn L.; Wiedner, Eric; Johnson, Marc J A.

In: Journal of the American Chemical Society, Vol. 129, No. 13, 04.04.2007, p. 3800-3801.

Research output: Contribution to journalArticle

Geyer, Andrea M. ; Gdula, Robyn L. ; Wiedner, Eric ; Johnson, Marc J A. / Catalytic nitrile-alkyne cross-metathesis. In: Journal of the American Chemical Society. 2007 ; Vol. 129, No. 13. pp. 3800-3801.
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