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One-pot Solvent-free Catalytic Dimerization Reaction of Phenylacetylene to 1-Phenylnaphthalene

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Abstract

In this study, we report a smooth one-pot, solvent-free catalytic dimerization of phenylacetylene (1) to 1-phenylnaphthalene (2) by Cu/C at room temperature in good yield (∼100%). In the computational study, the structure of the 1-phenylnaphthalene was optimized by DFT-B3LYP/6-31G* method. The rotation barrier around C-C of the phenyl and naphthalene parts of the molecule and its UV-Visible spectrum were calculated. The modelling of the mechanism of production of 2 from 1 was performed with and without Cu/C catalyst. The data of EDS and SEM of the Cu/C catalyst surface are also reported.

A smooth one-pot, solvent-free catalytic dimerization of phenylacetylene to 1-phenylnaphthalene by Cu/C catalyst at room temperature in good yield is reported. The structure of 1-phenylnaphthalene, C-C rotation barrier, UV-Visible spectrum and modelling of the dimerization mechanism with and without Cu/C were calculated by DFT-B3LYP/6-31G*. The EDS and SEM of Cu/C are reported as well.

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References

  1. Fetzer J C 2000 Polycycl. Aromat. Comp. 27 143

    Article  Google Scholar 

  2. Herwig P T, Enkelmann V, Schmelz O and Müllen K 2000 Chem. Eur. J. 6 1834

    Article  CAS  Google Scholar 

  3. Glenn R M 1995 In Activated carbon applications in the food and pharmaceutical industries (Boca Raton FL: CRC Press) p. 125

  4. Portella G, Poater J and Solà M 2005 J. Phys. Org. Chem. 18 785

    Article  CAS  Google Scholar 

  5. Luch A 2005 In The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons (London: Imperial College)

  6. Hawley G G 1997 In Condensed Chemical Dictionary 13 th Ed. (New York: Van Nostrand Reinhold Company Inc.)

  7. (a) Weiss R 1955 Org. Syntheses 3 729; (b) Chattaway F D 1893 J. Chem. Soc. 63 1187; (c) Weiss R and Woidich K 1925 Monatsh. Chem. 46 455; (d) Cook J W and Lawrence C A 1936 J. Chem. Soc. 11 1431; (e) Vesely V and Stursa F 1933 Collect. Czech. Chem. Commun. 5 344; (f) Orchin M and Reggel L 1947 J. Am. Chem. Soc. 69 505; (g) Grieve W S M and Hay D H 1938 J. Chem. Soc. 13 108; (h) Waters W H 1939 J. Chem. Soc. 14 864; (i) Hodgson H H and Marsden E 1940 J. Chem. Soc. 15 208; (j) Bachmann W E and Hofmann R A 1944 Org. Reac. 2 248

  8. Sun C L, Li H, Yu D G, Yu M, Zhou X, Lu X Y, Huang K, Zheng S F, Li B J and Shi Z J 2010 Nature Chem. 2 1044

    Article  CAS  Google Scholar 

  9. Firouzabadi H, Iranpoor N and Ghaderi A 2011 Org. Biomol. Chem. 9 865

    Article  CAS  Google Scholar 

  10. Sonogashira K, Tohda Y and Hagihara N 1975 Tetrahedron Lett. 16 4467

    Article  Google Scholar 

  11. Chinchilla R and Najera C 2007 Chem. Rev. 107 874

    Article  CAS  Google Scholar 

  12. Gil-Molto J and Najera C 2006 Adv. Synth. Catal. 348 1874

    Article  CAS  Google Scholar 

  13. Dudnik A and Gevorgyan V 2010 Angew. Chem. Int. Ed. 49 2096

    Article  CAS  Google Scholar 

  14. Cicero D, Lembo A, Leoni A and Tagliatesta P 2009 New J. Chem. 33 2162

    Article  CAS  Google Scholar 

  15. Vogel A 1986 In Vogel’s Textbook of Practical Organic Chemistry. Including qualitative organic analysis (4 th Ed). (England: Longman Group Limited)

  16. (a) Pouchert C L 1983 In The Aldrich Library of NMR Spectra (2th Ed.). (Milwaukee, Wisconsin: Aldrich Chemical Company Inc.) 1 pp. 2, 740-2, 762; (b) Pouchert C L 1981 In The Aldrich Library of Inferared Spectra 3th Ed. (Milwaukee, Wisconsin: Aldrich Chemical Company Inc.) pp. 27, 40-2, 578; (c) 1-phenylnaphthalene http://www.chemsynthesis.com/base/ chemical-structure-5127.html

  17. Spatran ’10-Quantum Mechanics Program: (PC/x86) 1.1.0 v4. 2011 (Irvine CA: Wavefunction Inc.)

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Acknowledgements

A T gratefully acknowledges the colleagues in Chemistry Department of The University of Queensland-Australia for their useful suggestions. The authors are grateful to the Research and Computational Lab of Theoretical Chemistry and Nano Structures of Razi University Kermanshah-Iran for supporting this study.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Razi University, P.O. Box: 67149-67346, Kermanshah, Iran

    AVAT (ARMAN) TAHERPOUR & AKO YARI

  2. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

    AVAT (ARMAN) TAHERPOUR

  3. Chemistry Department, Science Faculty, Islamic Azad University, Arak Branch, P.O. Box 38135-567, Arak, Iran

    SEPEHR TABAN

Authors
  1. AVAT (ARMAN) TAHERPOUR
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  2. SEPEHR TABAN
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Correspondence to AVAT (ARMAN) TAHERPOUR.

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Supplementary Information

1H-NMR spectra of phenyl-acetylene, 1-phenylnaphthalene (figures S1 and S2), EDS analysis (figure S3) and the SEM of Cu/C catalyst (figure S4) are shown in the Supplementary Information which is available at www.ias.ac.in/chemsci.

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TAHERPOUR, A.(., TABAN, S. & YARI, A. One-pot Solvent-free Catalytic Dimerization Reaction of Phenylacetylene to 1-Phenylnaphthalene. J Chem Sci 127, 1523–1530 (2015). https://doi.org/10.1007/s12039-015-0926-7

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  • DOI: https://doi.org/10.1007/s12039-015-0926-7

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