Pd/C应用很好的总结 / 开普饭

介绍和性质

[7440-05-3]· Pd · Palladium on Carbon · (MW 106.42)

(catalyst for hydrogenation of alkenes, alkynes, ketones, nitriles, imines, azides, nitro groups, benzenoid and heterocyclic aromatics; used for hydrogenolysis of cyclopropanes, benzyl derivatives, epoxides, hydrazines, and halides; used to dehydrogenate aromatics and deformylate aldehydes) Solubility:insol all organic solvents and aqueous acidic media. Form Supplied in:black powder or pellets containing 0.5-30 wt % of Pd (typically 5 wt %); can be either dry or moist (50 wt % of H2O). Analysis of Reagent Purity:atomic absorption. Handling, Storage, and Precautions:can be stored safely in a closed container under air but away from solvents and potential poisons such as sulfur- and phosphorus-containing compounds. Pyrophoric in the presence of solvents. General precautions for handling hydrogenation catalysts should be followed. The catalyst must be suspended in the organic solvent under an atmosphere of N2. During filtration the filter cake must not be allowed to go dry. If a filter aid is necessary, a cellulose-based material should be used if catalyst recovery is desired.

Hydrogenation and Hydrogenolysis: Carbon-Carbon Bonds

Carbon-Nitrogen Bonds

Carbon-Oxygen Bonds

Pd/C is best suited for the hydrogenation and hydrogenolysis ofbenzylic ketones and aldehydes. The reduction of dialkyl ketones to the alcohols is more sluggish and further hydrogenolysis to the alkane is even slower. The hydrogenation of benzylic ketones (aryl alkyl and diaryl ketones) to alcohols is a very facile process with Pd/C.Further hydrogenolysis of the benzylic alcohols to the alkane products can be a major problem with Pd/C catalysts, but can be controlled. In general, aryl ketones and aldehydes can be reduced to alcohols under neutral conditions or in the presenceof an amino functional group or an added amine base. In the presence of acids, hydrogenolysis is more prone to occur. Using other catalysts such as Platinum on CarbonRu/C, Rh/C and Raney Nickel, is an alternative.

Nitrogen-Oxygen Bonds

Carbon-Halogen Bonds

Nitrogen-Nitrogen Bonds

Carbocyclic and Heterocyclic Aromatics

Dehydrogenation

Miscellaneous Reactions

Reference

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N. A.; Heck, R. F. JOC 1978, 43, 3985. Olah, G. A.; Surya Prakash, G. K. S 1978, 397. (b) Baker, R.; Boyes, R. H. O.;

Broom, D. M. P.; O'Mahony, M. J.; Swain, C. J. JCS(P1) 1987, 1613. Cossy, J.; Pete, J.-P. BSF 1988, 989. Taylor, E.

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L. E. JACS 1987, 109, 6115.

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7. Tsuda, Y.; Hosoi, S.; Goto, Y. CPB 1991, 39, 18.

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JOC 1990, 55, 5336.

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11. Bock, K.; Lundt, I.; Pedersen, C. ACS 1981, 35, 155.

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13. Rylander, P. N.; Hasbrouck, L.; Karpenko, I. ANY 1973, 214, 100.

14. Bredereck, H.; Simchen G.; Traut, H. CB 1967, 100, 3664. Mizzoni, R. H.; Lucas, R. A.; Smith, R.; Boxer, J.; Brown,

J. E.; Goble, F.; Konopka, E.; Gelzer, J.; Szanto, J.; Maplesden, D. C.; deStevens, G. JMC 1970, 13, 878. Caluwe, P.;

Majewicz, T. G. JOC 1977, 42, 3410.

Pd/C应用很好的总结

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