Catalytic nitrile-alkyne cross-metathesis

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

doi:10.1021/ja0693439

Catalytic nitrile-alkyne cross-metathesis

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

Pacific Northwest National Laboratory

Research output: Contribution to journal › Article › peer-review

47 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

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Catalytic nitrile-alkyne cross-metathesis",

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).",

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AU - Geyer, Andrea M.

AU - Gdula, Robyn L.

AU - Wiedner, Eric S.

AU - Johnson, Marc J.A.

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N2 - 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).

AB - 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).

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