Ring-Closing Alkyne Metathesis (RCAM)

By: Dr. Josephine Nakhla, Chemfiles Volume 10 Article 1

Alkyne metathesis has been a useful tool for C–C bond formation since the discovery of structurally well-defined metal alkylidynes by Schrock and coworkers.2 These complexes have found use in the synthesis of complex natural products and in material science.3 The limitations of these catalysts include air- and moisture-sensitivity as well as incompatibilities with substrates that contain donor sites. Fürstner and co-workers have recently developed an air-stable molybdenum catalyst for alkyne metathesis, which proved versatile and compatible with substrates containing donor sites.4 The authors also examined the use of this catalyst in the ring-closing cross metathesis (RCAM) of a variety of alkynes in generating various macrocycles in good yields (Scheme 3).

Scheme 3: Air-Stable molybdenum catalyst for alkyne metathesis.


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Materials

     

References

  1. (a) Romero, P. E. et al. Angew. Chem. Int. Ed. 2004, 43, 6161. (b) Romero, P. E.; Piers, W. E. J. Am. Chem. Soc. 2005, 127, 5032.
  2. Schrock, R. R. Chem. Rev. 2002, 102, 145.
  3. (a) Fürstner, A. et al. Chem. Commun. 2005, 2307. (b) Schrock, R. R. et al. Adv. Synth. Catal. 2007, 349, 55.
  4. Bindl, M. et al. J. Am. Chem. Soc. 2009, 131, 9468.

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