In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Ruthenium-Catalyzed [2 + 2] Cycloadditions between 7-Substituted Norbornadienes and Alkynes: An Experimental and Theoretical Study, published in 2004-11-26, which mentions a compound: 92390-26-6, mainly applied to ruthenium catalysis cycloaddition norbornadiene alkyne experiment theor, Quality Control of Chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium.
The ruthenium-catalyzed [2 + 2] cycloadditions of 7-substituted norbornadienes with an alkyne have been investigated. The cycloadditions were found to be highly regio- and stereoselective, giving only the anti-exo cycloadducts as the single regio- and stereoisomers in good yields. The results on the relative rate of different 7-substituted norbornadienes in the Ru-catalyzed [2 + 2] cycloadditions with an alkyne indicated that the reactivity of the alkene component decreases dramatically as the alkene becomes more electron deficient. Ab initio computational studies on the ruthenium-catalyzed [2 + 2] cycloadditions provided important information about the geometries and the arrangements of the four different groups on the Ru in the initial Ru-alkene-alkyne π-complex, 14, and in the metallacyclopentene 15. Based on our computational studies, we also found that the first carbon-carbon bond formed in the [2 + 2] cycloaddition is between the C5 of the alkene and the Cb (the acetylenic carbon attached to the ester group) of the alkyne 8. Our computational studies on the potential energy profiles of the cycloadditions showed that the activation energy relative to the reactants for the oxidative addition step is in the range of 9.3-9.8 kcal/mol. The activation energy relative to the metallacyclopentene for the reductive elimination step is much higher than for the oxidative addition step (in the range of 25.9-27.6 kcal/mol).
In addition to the literature in the link below, there is a lot of literature about this compound(Chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium)Quality Control of Chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium, illustrating the importance and wide applicability of this compound(92390-26-6).
Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method