Selective semi-hydrogenation of propargylamines using palladium magnetic nanocatalyst

Selective semi-hydrogenation of propargylamines using palladium magnetic nanocatalyst

Uberman, Paula M.; Costa, Natalia J. S.; Albuquerque, Joao L. P.; Santos, Alcindo A. Dos; Rossi, Liane M.

Abstract:

Selective hydrogenation of alkynes is an important transformation in organic synthesis and, the development of methodologies to obtain olefins is still challenging. Nowadays, there is a growing demand for process that allows transformations on highly functionalized molecules as synthetic intermediates for pharmaceutical products. In that sense, the preparation and modification of propargylamines has gained popularity in recent years. Propargylamine derivates can be synthesized by A3 coupling, which is a multicomponent reaction between an aldehyde, an amine and an alkyne. Palladium is the most widely used catalysts to perform hydrogenation of alkynes but the evaluation of the catalytic activity and selectivity of new catalysts is usually made with simple alkynes. Herein, we report the synthesis of functionalized propargylamines, and the development of new highly active and selective magnetic Pd nanocatalyst to perform the partial hydrogenation of these compounds. In the last ten years, the use of magnetic nanoparticles (MNPs) as catalyst supports brought a new perception of catalysis in terms activity, selectivity and sustainability. However, Pd supported on MNPs still remains scarcely explored in the hydrogenation of alkynes.

Selective hydrogenation of alkynes is an important transformation in organic synthesis and, the development of methodologies to obtain olefins is still challenging. Nowadays, there is a growing demand for process that allows transformations on highly functionalized molecules as synthetic intermediates for pharmaceutical products. In that sense, the preparation and modification of propargylamines has gained popularity in recent years. Propargylamine derivates can be synthesized by A3 coupling, which is a multicomponent reaction between an aldehyde, an amine and an alkyne. Palladium is the most widely used catalysts to perform hydrogenation of alkynes but the evaluation of the catalytic activity and selectivity of new catalysts is usually made with simple alkynes. Herein, we report the synthesis of functionalized propargylamines, and the development of new highly active and selective magnetic Pd nanocatalyst to perform the partial hydrogenation of these compounds. In the last ten years, the use of magnetic nanoparticles (MNPs) as catalyst supports brought a new perception of catalysis in terms activity, selectivity and sustainability. However, Pd supported on MNPs still remains scarcely explored in the hydrogenation of alkynes.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201310419485

Referências bibliográficas

• [1] 1 Crespo-Quesada, M.; Cardenas-Lizana, F.; Dessimoz, A. L.; Kiwi-Minsker, L. ACS Catal. 2012, 2, 1773
• [2] 2 Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790
• [3] 3 J. S. Costa, PhD Thesis, São Paulo University, 2012.
• [4] 4 Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Chem. Rev. 2011, 111, 3036

Como citar:

Uberman, Paula M.; Costa, Natalia J. S.; Albuquerque, Joao L. P.; Santos, Alcindo A. Dos; Rossi, Liane M.; "Selective semi-hydrogenation of propargylamines using palladium magnetic nanocatalyst", p-32-32. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201310419485