Ring-Closing Alkyne Metathesis (RCAM)

By: William Sommer, Aldrich ChemFiles 2009, 9.6, 6.

Aldrich ChemFiles 2009, 9.6, 6.

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.1 These complexes have found use in the synthesis of complex natural products and in material science.2 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.3 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 9).

Scheme 9

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Materials

     

References

  1. Schrock, R. R. Chem. Rev. 2002, 102, 145.
  2. (a)Fürstner, A. et al. Chem. Commun. 2005, 2307. (b) Schrock, R. R. et al. Adv. Synth. Catal. 2007, 349, 55.
  3. Bindl, M. et al. J. Am. Chem. Soc. 2009, 131, 9468.

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