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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 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
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]
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.
An example of this is the Tsuji–Wilkinson decarbonylation reaction using Wilkinson's catalyst. (Strictly speaking, the noncatalytic version of this reaction results in the formation of a rhodium carbonyl complex rather than free carbon monoxide.)
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 ...
Wilkinson's catalyst is used as a homogeneous catalyst for the hydrogenation of olefins. [9] The mechanism of catalysis involves oxidative addition of H 2, π-complexation of alkene, migratory insertion (intramolecular hydride transfer or olefin insertion), and reductive elimination.
Dehydrogenative coupling of primary silanes using Wilkinson's catalyst is slow and dependent on the removal of H 2 product. This conversion proceeds by oxidative addition of the Si-H bond and elimination of dihydrogen. [7] Tris(pentafluorophenyl)borane (B(C 6 F 5) 3)) is yet another catalyst for the dehydrogenative coupling of tertiary silanes ...