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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]
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.
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 ]
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.
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.
[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 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
Catalyst prepared and handled under anaerobic condition reverses the selectivity to favor the secondary boronate ester. What has been debated is the coordination of the alkene. In the dissociative mechanism, proposed by Männig and Nöth, [ 4 ] and supported by Evans and Fu [ 5 ] the coordination is accompanied by the loss of one ...