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Dehydrogenation of 2-Phenyl-1-pyrroline with Palladium-Supported Catalysts: An Effective Route to the Synthesis of 2-Phenylpyrrole

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Abstract

The catalytic dehydrogenation of 5-phenyl-3,4-dihydro-2H-pyrrole (2-phenyl-1-pyrroline) to 2-phenyl-1H-pyrrole in the presence of palladium-supported on activated carbon (Pd/C) or on alumina (Pd/Al2O3) is reported. Highly pure 2-phenylpyrrole is obtained in good yields and selectivities, in a ca. 20 gram-scale, after a simple work-up. The Pd/Al2O3 catalyst exhibited substantially higher activities than the Pd/C ones.

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Acknowledgments

The authors thank the Fundação para a Ciência e Tecnologia for financial support (Projects PTDC/EQU–EQU/110313/2009, PEst-OE/QUI/UI0100/2013 and RECI/QEQ-QIN70189/2012) and for a fellowship to C.A.F. (SFRH/BD/47730/2008). We also thank Dr. R. C. Neto (IDMEC-IST) and to Mr. P. F. Mendes (CQE-IST) for their valuable help in the analysis of molecular hydrogen in the gas phase and of the reaction components by gas chromatography, respectively.

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Authors and Affiliations

  1. Centro de Química Estrutural, Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1, 1049-001, Lisboa, Portugal

    Cláudia A. Figueira & Pedro T. Gomes

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  1. Cláudia A. Figueira
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  2. Pedro T. Gomes
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Correspondence to Pedro T. Gomes.

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Figueira, C.A., Gomes, P.T. Dehydrogenation of 2-Phenyl-1-pyrroline with Palladium-Supported Catalysts: An Effective Route to the Synthesis of 2-Phenylpyrrole. Catal Lett 145, 762–768 (2015). https://doi.org/10.1007/s10562-014-1469-0

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