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Abstract: The development of efficient method for the construction of new carbon-carbon bond through olefin-olefin metathesis continues to an important goal for the synthetic organic chemistry. Making new carbon-carbon bond through carbonyl olefin metathesis reaction is limited but has recently attracted significant interest and attraction. Most popularly transition metal complexes were used as catalyst for carbonyl-olefin metathesis1, but it has many limitations. The use of stoichiometric amount of transition metal and formation of kinetically inert metal oxo species prevent the regeneration of active catalyst. In this regard various synthetic strategies have been adopted for metal free carbonyl olefin metathesis. Which includes cycloaddition2, Bronsted acid3 and Lewis acid4 mediated carbonyl-olefin metathesis and carbocation promoted5 carbonyl olefin metathesis.

References:

  1. Fu, G. C.; Grubbs, R. H., Synthesis of cycloalkenes via alkylidene-mediated olefin metathesis and carbonyl olefination. J Am Chem Soc 1993, 115 (9), 3800-3801.
  2. Griffith, A. K.; Vanos, C. M.; Lambert, T. H., Organocatalytic Carbonyl-Olefin Metathesis. J Am Chem Soc 2012, 134 (45), 18581-18584.
  3. Vanschaik, H. P.; Vijn, R. J.; Bickelhaupt, F., Acid-Catalyzed Olefination of Benzaldehyde. Angewandte Chemie-International Edition in English 1994, 33 (15-16), 1611-1612.
  4. Soicke, A.; Slavov, N.; Neudorfl, J. M.; Schmalz, H. G., Metal-Free Intramolecular Carbonyl-Olefin Metathesis of ortho-Prenylaryl Ketones. Synlett 2011, (17), 2487-2490.
  5. Ni, S. J.; Franzen, J., Carbocation catalysed ring closing aldehyde-olefin metathesis. Chem Commun 2018, 54 (92), 12982-12985.