A Facile and Inexpensive Synthesis of 6-Ethynylbipyridine
Jianqiang Huo, John O. Hoberg
.
DOI: 10.4236/ijoc.2011.12006   PDF    HTML     6,390 Downloads   12,758 Views  

Abstract

An inexpensive synthesis of 6-ethynylbipyridine has been accomplished using Sonogashira coupling of 2-bromo-6-iodopyridine with 2-methyl-3-butyn-2-ol. Subsequent Stille coupling with 2-(trimethylstannanyl) pyridine and hydrolysis provided the target compound in an overall high yield.

Share and Cite:

J. Huo and J. Hoberg, "A Facile and Inexpensive Synthesis of 6-Ethynylbipyridine," International Journal of Organic Chemistry, Vol. 1 No. 2, 2011, pp. 33-36. doi: 10.4236/ijoc.2011.12006.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] S. T. Gaballah, C. E. Kerr, B. E. Eaton and T. L. Netzel, Nucleosides, Nucleotides Nucleic Acids, Vol. 21, 2002, pp. 547-560.
[2] (a) M. Vrabel, M. Hocek, L. Havran, M. Fojta, I. Votruba, B. Klepetarova, R. Pohl, L. Rulisek, L. Zendlova, P. Hobza, I. Shih, E. Mabery, R. Mackman, Eur. J. Inorg. Chem. 2007, pp. 1752-1769. (b) M. Vrabel, R. Pohl, B. Klepetarova, I. Votruba, M. Hocek, Org. Biomol. Chem. Vol. 5, 2007, pp. 2849-2857. (c) M. Vrabel, I. Rosenberg, M. Hocek, Collect. Symp. Ser. Vol. 7, 2005, pp. 485-486.
[3] Our use of 1 is in this area and others have used isomers of 1 as photoactive materials, for use of these isomers see: (a) T. Pautzsch, E. Klemm, Macromolecules Vol. 35, 2002, pp. 1569-1575. (b) A. Ambroise, R. W. Wagner, P. D. Rao, J. A. Riggs, P. Hascoat, J. R. Diers, J. Seth, R. K. Lammi, D. F. Bocian, D. Holten, J. S. Lindsey, Chem. Mater. Vol. 13, 2001, pp. 1023-1034. (c) M. Hissler, R. Ziessel, New J. Chem. Vol. 21, 1997, pp. 843-846. (d) V. Grosshenny, F. M. Romero, R. Ziessel, J. Org. Chem. Vol. 62,
[4] N. A. Jones, J. W. Antoon, A. L. Bowie, J. B. Borak, E. P. Stevens, J. Heterocyclic Chem. Vol. 44, 2007, pp. 363-367.
[5] F. Trecourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Queguiner, Tetrahedron Vol. 56, 2000, pp. 1349-1360.
[6] M. A. Peterson, J. R. Mitchell, J. Org. Chem. Vol. 62, 1997, pp. 8237-8239.
[7] P. F. H. Schwab, F. Fleischer, J. Michl, J. Org. Chem. Vol. 67, 2002, pp. 443-449.
[8] (a) Y. Takayama, T. Hanazawa, T. Andou, K. Muraoka, H. Ohtani, M. Takahashi, and F. Sato, Org. Lett., Vol. 6, 2004, 4253-4256. (b) N. Pagano, J. Maksimoska, H. Bregman, D.S. Williams, R.D. Webster, F. Xue, and E. Meggers, Org. Biomol. Chem., Vol. 5, 2007, 1218-1227. (c) B.T. Holmes, W.T. Pennington, and T.W. Hanks, Molecules, Vol. 7, 2002, 447-455. (d) F. Cottet and M. Schlosser, Eur. J. Org. Chem., 2002, 327-330. (e) M. Benaglia, F. Ponzini, C.R. Woods, and J.S. Siegel, Org. Lett. Vol. 3, 2001, 967-969.

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.