Pauson–Khand reaction

Pauson–Khand reaction

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.Ref|1Ref|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The original catalyst for this organic reaction was dicobalt octacarbonyl but this has since been replaced by other catalyst systems.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 Ref|3.

Molybdenum hexacarbonyl is a carbon monoxide donor in PK-type reactions between allenes and alkynes with dimethyl sulfoxide in toluene Ref|4.

Cyclobutadiene als lends itself to a [2+2+1] cycloaddition although this reactant is generated in situ from decomplexation of stable cyclobutadiene iron tricarbonyl with CAN. Ref|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. ( [http://www.iupac.org/publications/pac/2002/pdf/7401x0085.pdf Online article] )
# "A New Allenic Pauson-Khand Cycloaddition for the Preparation of a-Methylene Cyclopentenones" Joseph L. Kent, Honghe Wan and Kay M. Brummond ( [http://www.pitt.edu/~kbrummon/Pubspdfs/paper.pdf 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)

ee also

*Nicholas reaction


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