The process of hydrogenation can be carried out step by step, and at the stage of intermediate alkene, it can be halted using modified catalysts like the Lindlar catalyst. Comprising palladium deposited on calcium carbonate and treated with lead acetate and quinoline, this catalyst undergoes alterations on its surface, adopting a less active configuration compared to palladium on carbon. This configuration enables the selective hydrogenation of only the first π bond of the alkyne. Similar to the catalytic hydrogenation of alkenes, the addition of H2 is a syn process. Consequently, this technique enables the stereoselective synthesis of cis alkenes from alkynes.
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References :
[1]Stachurski J, Thomas J M. Structural aspects of the lindlar catalyst for selective hydrogenation[J]. Catalysis letters, 1988, 1(1-3): 67-72.
[2]Cherkasov N, Murzin D Y, Catlow C R A, et al. Selectivity of the Lindlar catalyst in alkyne semi-hydrogenation: a direct liquid-phase adsorption study[J]. Catalysis Science & Technology, 2021, 11(18): 6205-6216.
[3]Ghosh A K, Krishnan K. Chemoselective catalytic hydrogenation of alkenes by Lindlar catalyst[J]. Tetrahedron letters, 1998, 39(9): 947.
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