Catalytic nitrile-alkyne cross-metathesis

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

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43 Citations (Scopus)

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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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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