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. This reaction was originally mediated by stoichiometric amounts of dicobalt octacarbonyl, but this has since been replaced by newer and more efficient catalyst systems.
The reaction works with both terminal and internal alkynes although internal alkynes tend to give lower yields. The order of reactivity for the alkene is strained cyclic alkene > terminal alkene > disubstituted alkene > trisubstituted alkene. Unsuitable alkenes are tetrasubstituted alkenes and alkenes with strongly electron withdrawing groups.
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- Pauson–Khand-type reaction mediated by Rh(I) catalysts 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)
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- 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