The Pauson–Khand reaction (or PKR or PK-type reaction) is a chemical reaction described as a [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form a α,β-cyclopentenone.[1][2] The original catalyst for this organic reaction was dicobalt octacarbonyl but this has since been replaced by other catalyst systems.
With asymmetrical alkenes or alkynes regioselectivity is always an issue, but less so with intramolecular reactions .
Variations
Wilkinson's catalyst based on the transition metal rhodium also effectively catalyses PK reactions but requires silver triflate as a co-catalyst [3].
Molybdenum hexacarbonyl is a carbon monoxide donor in PK-type reactions between allenes and alkynes with dimethyl sulfoxide in toluene [4].
Cyclobutadiene also lends itself to a [2+2+1] cycloaddition although this reactant is generated in situ from decomplexation of stable cyclobutadiene iron tricarbonyl with CAN. [5].
References
- ^ P. L. Pauson and I. U. Khand. Ann. N.Y. Acad. Sci. 1977, 295, 2.
- ^ Blanco-Urgoiti, J.; Añorbe, L.; Pérez-Serrano, L.; Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2004, 33, 32. (doi:10.1039/b300976a)
- ^ Nakcheol Jeong, Byung Ki Sung, Jin Sung Kim, Soon Bong Park,Sung Deok Seo, Jin Young Shin, Kyu Yeol In, and Yoon Kyung Choi Pure Appl. Chem., Vol. 74, No. 1, pp. 85–91, 2002. (Online article)
- ^ A New Allenic Pauson-Khand Cycloaddition for the Preparation of a-Methylene Cyclopentenones Joseph L. Kent, Honghe Wan and Kay M. Brummond (Online Article)
- ^ Intramolecular [2+2+1] Cycloadditions with (Cyclobutadiene)tricarbonyliron Benjamin A. Seigal, Mi Hyun An, Marc L. Snapper Angewandte Chemie International Edition Volume 44, Issue 31 , Pages 4929 - 4932 2005. (doi:10.1002/anie.200501100)
See also
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