Catalytic nitrile-alkyne cross-metathesis

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

doi:10.1021/ja0693439

Catalytic nitrile-alkyne cross-metathesis

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

Pacific Northwest National Laboratory

Research output: Contribution to journal › Article

42 Citations (Scopus)

Abstract

The first catalytic cross-metathesis reaction of an alkyne with a nitrile is described. The nitride complex N_≡W(OC(CF₃)₂CH₃)₃(DME) undergoes reversible triple-bond metathesis reactions with alkynes (RC_≡CR; R = Et, 4-C₆H₄OMe), forming the alkylidyne complexes RC_≡W(OC(CF₃)₂CH₃)₃(DME) (R = Et, 4-C₆H₄OMe) along with the corresponding nitrile RC_≡N. 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 language	English
Pages (from-to)	3800-3801
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	13
DOIs	https://doi.org/10.1021/ja0693439
Publication status	Published - Apr 4 2007

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Nitriles

Alkynes

Nitrides

Byproducts

Atoms

Cross Reactions

ASJC Scopus subject areas

Chemistry(all)

Cite this

Geyer, A. M., Gdula, R. L., Wiedner, E., & Johnson, M. J. A. (2007). Catalytic nitrile-alkyne cross-metathesis. Journal of the American Chemical Society, 129(13), 3800-3801. https://doi.org/10.1021/ja0693439

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 journal › Article

Geyer, AM, Gdula, RL, Wiedner, E & Johnson, MJA 2007, 'Catalytic nitrile-alkyne cross-metathesis', Journal of the American Chemical Society, vol. 129, no. 13, pp. 3800-3801. https://doi.org/10.1021/ja0693439

Geyer AM, Gdula RL, Wiedner E, Johnson MJA. Catalytic nitrile-alkyne cross-metathesis. Journal of the American Chemical Society. 2007 Apr 4;129(13):3800-3801. https://doi.org/10.1021/ja0693439

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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10.1021/ja0693439