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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  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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