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Wilkinson's catalyst is best known for catalyzing the hydrogenation of olefins with molecular hydrogen. [ 11 ] [ 12 ] The mechanism of this reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively, followed by oxidative addition of H 2 to the metal.
The difference in regioselectivity is more pronounced in the hydroboration of vinylarenes with HBcat. Wilkinson's catalyst or the cation Rh(COD) 2 (in the presence of PPh 3) produces the Markovnikov product. [12] [13] The anti-Markovnikov product is produced in the absence of a catalyst. [14]
Mechanism for the hydrogenation of a terminal alkene using Wilkinson's catalyst. Homogeneous catalysts are also used in asymmetric synthesis by the hydrogenation of prochiral substrates. An early demonstration of this approach was the Rh-catalyzed hydrogenation of enamides as precursors to the drug L-DOPA. [10]
The Tsuji–Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides. The reaction name recognizes JirÅ Tsuji, whose team first reported the use of Wilkinson's catalyst (RhCl(PPh 3) 3) for these reactions: RC(O)X + RhCl(PPh 3) 3 → RX + RhCl(CO)(PPh 3) 2 + PPh 3
Karstedt's catalyst was later introduced. It is a lipophilic complex that is soluble in the organic substrates of industrial interest. [10] Complexes and compounds that catalyze hydrogenation are often effective catalysts for hydrosilylation, e.g. Wilkinson's catalyst.
The reaction is not widely practiced in part because the alkanes are less useful materials than are the aldehyde precursors. Furthermore, the reaction is not often conducted catalytically because the extruded CO can be slow to dissociate. [9] Extrusion of CO from an organic aldehyde is most famously demonstrated using Wilkinson's catalyst: [10]
The reaction required tin tetrachloride and a stoichiometric amount of Wilkinson's catalyst: An equal amount of a cyclopropane was formed as the result of decarbonylation. The first catalytic application involved cyclization of 4-pentenal to cyclopentanone using (again) Wilkinson's catalyst. [4] In this reaction the solvent was saturated with ...
Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity.Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction.