The heterogeneous hydrogenation of substituted pyridines has been accomplished by employing a continuous flow hydrogenation device that incorporates in situ hydrogen generation by electrolysis of H20 and pre-packed catalyst cartridges. In general, the hydrogenation reactions proceeded smoothly regardless of the supported precious metal catalyst (Pd/C, Pt/C, or Rh/C). By using 30-80 bar of hydrogen pressure at 60-80 °C full conversion was typically achieved in all cases at a flow rate of 0.5 mL min -1, providing the corresponding piperidines in high yields. For disubstituted pyr idines, variations in stereoselectivity were observed depending on both the metal catalyst and the temperature/ pressure of the hydrogenation reaction. For ethyl nicotinate the selectivity between partial and full hydrogenation could be tuned depending on the hydrogen pressure, solvent, and the choice of supported metal catalyst. Changing the hydrogen source from H20 to D2C) allowed the preparation of de-uteriated derivatives. © Wiley-VCH Verlag GmbH & Co. KGaA.

Irfan, M., Petricci, E., Glasnov, T.N., Taddei, M., Kappe, C.O. (2009). Continuous Flow Hydrogenation of Functionalized Pyridines. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009(9), 1327-1332 [10.1002/ejoc.200801131].

Continuous Flow Hydrogenation of Functionalized Pyridines

Petricci, Elena;Taddei, Maurizio;
2009-01-01

Abstract

The heterogeneous hydrogenation of substituted pyridines has been accomplished by employing a continuous flow hydrogenation device that incorporates in situ hydrogen generation by electrolysis of H20 and pre-packed catalyst cartridges. In general, the hydrogenation reactions proceeded smoothly regardless of the supported precious metal catalyst (Pd/C, Pt/C, or Rh/C). By using 30-80 bar of hydrogen pressure at 60-80 °C full conversion was typically achieved in all cases at a flow rate of 0.5 mL min -1, providing the corresponding piperidines in high yields. For disubstituted pyr idines, variations in stereoselectivity were observed depending on both the metal catalyst and the temperature/ pressure of the hydrogenation reaction. For ethyl nicotinate the selectivity between partial and full hydrogenation could be tuned depending on the hydrogen pressure, solvent, and the choice of supported metal catalyst. Changing the hydrogen source from H20 to D2C) allowed the preparation of de-uteriated derivatives. © Wiley-VCH Verlag GmbH & Co. KGaA.
2009
Irfan, M., Petricci, E., Glasnov, T.N., Taddei, M., Kappe, C.O. (2009). Continuous Flow Hydrogenation of Functionalized Pyridines. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009(9), 1327-1332 [10.1002/ejoc.200801131].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/9132
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