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The hydrogenation of alkynes is troublesome to control since alkynes tend to be reduced to alkanes, via intermediacy of the cis-alkene. [14] Ethylene reacts with Wilkinson's catalyst to give RhCl(C 2 H 4)(PPh 3) 2, but it is not a substrate for hydrogenation. [10]
Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces double and triple bonds in hydrocarbons. [1]
Crabtree's catalyst is an organoiridium compound with the formula [C 8 H 12 IrP(C 6 H 11) 3 C 5 H 5 N]PF 6.It is a homogeneous catalyst for hydrogenation and hydrogen-transfer reactions, developed by Robert H. Crabtree.
A Lindlar catalyst is a heterogeneous catalyst consisting of palladium deposited on calcium carbonate or barium sulfate then poisoned with various forms of lead or sulfur. It is used for the hydrogenation of alkynes to alkenes (i.e. without further reduction into alkanes). It is named after its inventor Herbert Lindlar, who discovered it in 1952.
Wilkinson's catalyst, RhCl(PPh 3) 3 is a square planar Rh(I) complex of historical significance used to catalyze the hydrogenation of alkenes. Vaska's complex, trans-IrCl(CO)(PPh 3) 2, is also historically significant; it was used to establish the scope of oxidative addition reactions.
The process is mechanistically similar to the hydrogenation of alkenes. In fact, similar catalysts are sometimes employed for the two catalytic processes. The prevalent mechanism, called the Chalk-Harrod mechanism, assumes an intermediate metal complex that contains a hydride, a silyl ligand (R 3 Si), and the alkene
[4] [5] Hydrogenation occurs with syn stereochemistry when used on an alkyne resulting in a cis-alkene. Some of the most important transformations include the hydrogenation of ketones to alcohols or ethers (the latter product forming in the presence of alcohols and acids) [ 6 ] and the reduction of nitro compounds to amines. [ 7 ]
The insertion of alkenes into metal-hydrogen bonds is a key step in hydrogenation and hydroformylation reactions. The reaction involves the alkene and the hydride ligands combining within the coordination sphere of a catalyst. In hydrogenation, the resulting alkyl ligand combines with a second hydride to give the alkane.