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.
Graphical Abstract
Similar content being viewed by others
References
Estévez V, Villacampa M, Menendez JC (2010) Chem Soc Rev 39:4402
Burghart A, Kim H, Welch MB, Thoresen LH, Reibenspies J, Burgess KJ (1999) Org Chem 64:7813
Bonnet R, Motevalli M, Siu J (2004) Tetrahedron 60:8913
Stemp G, Johnson CN (1997) U.S. Patent 5 637 609
Knight LW, Huffman JW, Isherwood ML (2003) Synlett 1993
Uhr H, Marhold A, Böhm S, Erdelen C, Wachendorff-Neumann U, Stendel W (1995) U.S. Patent 5 378 724
Hewton CE, Kimber MC, Taylor DK (2002) Tetrahedron Lett 43:3199
Burns SA, Corriu RJP, Huynh V, Moreau JJE (1987) J Organomet Chem 333:281
Boukou-Poba JP, Farnier M, Guilard R (1979) Tetrahedron Lett 20:1717
Dhanak D, Reese CB, Romana S, Zappia G (1986) J Chem Soc Chem Commun 903
Ellames GJ, Hewkin CT, Jackson RFW, Smith DI, Standen SP (1989) Tetrahedron Lett 30:3471
de Kimpe N, Tehrani KA, Stevens C, de Cooman P (1997) Tetrahedron 53:3693
Xu Z, Lu X (1998) J Org Chem 63:5031
Yada Y, Miyake Y, Nishibayashi Y (2008) Organometallics 27:3614
Sukawa H, Seshimoto O, Tekuza T, Mukai T (1974) J Chem Soc Chem Commun 696
von der Saal W, Reinhardt R, Stawitz J, Quast H (1998) Eur J Org Chem 1645
Schmidt EY, Mikhaleva AI, Vasil’tsov AM, Zaitsev AB, Zorina NV (2005) Arkivoc vii:11
Mikhaleva AI, Petrova OV, Sobenina LN (2011) Chem Heterocycl Compd 47:1367
Filippini L, Gusmeroli M, Riva R (1992) Tetrahedron Lett 33:1755
Johnson CN, Stemp G, Anand N, Stephen SC, Gallagher T (1998) Synlett 1025
Rieth RD, Mankad NP, Calimano E, Sadighi JP (2004) Org Lett 6:3981
Jafarpour F, Rahiminejadan S, Hazrati H (2010) J Org Chem 75:3109
Bheeter CB, Bera JK, Doucet H (2012) Tetrahedron Lett 53:509
Craig L, Bulbrook H, Hixon RM (1931) J Am Chem Soc 53:1831
Adkins H, Lundsted LG (1949) J Am Chem Soc 71:2964
Wawzonek S, Hansen GR (1966) J Org Chem 31:3580
Carabineiro SA, Bellabarba RM, Gomes PT, Fonseca IM (2006) Catal Lett 111:221
Haneda S, Okui A, Ueba C, Hayashi M (2007) Tetrahedron 63:2414
Tanaka T, Okunaga K, Hayashi M (2010) Tetrahedron Lett 51:4633
Laidler KJ (1976) Chemical Kinetics. Tata McGraw-Hill, New Delhi, p 267
http://www.sigmaaldrich.com/spectra/fnmr/FNMR001311.PDF. Last access: 27th Dec 2014 at Sigma-Aldrich website
Resasco DE (2003) In: Horvath IT (ed) Dehydrogenation – Heterogeneous, Encyclopedia of Catalysis, Vol. 3. Wiley, New York, p 49
Rahaman MV, Vannice MA (1991) J Catal 127:251
Gomez R, del Angel G, Bertin V (1991) React Kinet Catal Lett 44:517
del Angel G, Bertin V, Perez A, Gomez R (1992) React Kinet Catal Lett 48:259
Arcoya A, Seoane XL, Gómez-Sainero LM (2003) Appl Surf Sci 211:341
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.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-014-1469-0