Skip to main content
SpringerLink
Log in

Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Palladium-catalyzed oxidative homocoupling of terminal acetylenes, in air, occurred in the presence of 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene as ligand, affording the corresponding conjugated diynes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. F. Diederich, P.J. Stang, R.R. Tykwinski (eds.), Acetylene Chemistry; Chemistry, Biology, and Material Science (Wiley–VCH, Weinheim, 2005)

    Google Scholar 

  2. P. Siemsen, R.C. Livingston, F. Diederich, Angew. Chem. Int. Ed. 39, 2632 (2000)

    Article  CAS  Google Scholar 

  3. A.L.K.S. Shun, R.R. Tykwinski, Angew. Chem. Int. Ed. 45, 1034 (2006)

    Article  CAS  Google Scholar 

  4. S. Kramer, J.L.H. Madsen, M. Rottländer, T. Skrydstrup, Org. Lett. 12, 2758 (2010)

    Article  CAS  Google Scholar 

  5. X. Fu, J. Chen, G. Li, Y. Liu, Angew. Chem. Int. Ed. 48, 5500 (2009)

    Article  CAS  Google Scholar 

  6. G. Nishida, S. Ogaki, Y. Yusa, T. Yokozawa, K. Noguchi, K. Tanaka, Org. Lett. 10, 2849 (2008)

    Article  CAS  Google Scholar 

  7. V. Lavallo, G.D. Frey, B. Donnadieu, M. Soleilhavoup, G. Bertrand, Angew. Chem. Int. Ed. 47, 5224 (2008)

    Article  CAS  Google Scholar 

  8. Y. Liu, H. Gao, S. Zhou, Angew. Chem. Int. Ed. 45, 4163 (2006)

    Article  CAS  Google Scholar 

  9. E.J. Cho, D. Lee, J. Am. Chem. Soc. 129, 6692 (2007)

    Article  CAS  Google Scholar 

  10. C.-W. Cho, M. Krische, J. Org. Lett. 8, 3873 (2006)

    Article  CAS  Google Scholar 

  11. X. Nie, G. Wang, J. Org. Chem. 71, 4734 (2006)

    Article  CAS  Google Scholar 

  12. T. Shimada, Y. Yamamoto, J. Am. Chem. Soc. 125, 6646 (2003)

    Article  CAS  Google Scholar 

  13. K.R. Deaton, M.S. Gin, Org. Lett. 5, 2477 (2003)

    Article  CAS  Google Scholar 

  14. M.S. Maji, T. Pfeifer, A. Studer, Angew. Chem. Int. Ed. 47, 9547 (2008)

    Article  CAS  Google Scholar 

  15. M.W. Paixão, M. Weber, A.L. Braga, J.B. de Azeredo, A.M. Deobald, H.A. Stefani, Tetrahedron Lett. 49, 2366 (2008)

    Article  Google Scholar 

  16. W. Shi, Y. Luo, X. Luo, L. Chao, H. Zhang, J. Wang, A. Lei, J. Am. Chem. Soc. 130, 14713 (2008)

    Article  CAS  Google Scholar 

  17. M. Alami, F. Ferri, Tetrahedron Lett. 37, 2763 (1996)

    Article  CAS  Google Scholar 

  18. A.S. Hay, J. Org. Chem. 27, 3320 (1962)

    Article  CAS  Google Scholar 

  19. C. Glaser, Ber. Dtsch. Chem. Ges. 2, 422 (1869)

    Article  Google Scholar 

  20. C. Ye, J.-C. Xiao, B. Twamley, A.D. LaLonde, M.G. Norton, J.M. Shreeve, Eur. J. Org. Chem. 30, 5095 (2007)

    Google Scholar 

  21. A.S. Batsanov, J.C. Collings, I.J.S. Fairlamb, J.P. Holland, J.A.K. Howard, Z. Lin, T.B. Marder, A.C. Parsons, R.M. Ward, J. Zhu, J. Org. Chem. 70, 703 (2005)

    Article  CAS  Google Scholar 

  22. Q. Liu, D.J. Burton, Tetrahedron Lett. 38, 4371 (1997)

    Article  CAS  Google Scholar 

  23. M. Bandini, R. Luque, V. Budarin, D.J. Macquarrie, Tetrahedron 61, 9860 (2005)

    Article  CAS  Google Scholar 

  24. S. Atobe, M. Sonoda, Y. Suzuki, H. Shinohara, T. Yamamoto, A. Ogawa, Chem. Lett. 40, 925 (2011)

    Article  CAS  Google Scholar 

  25. Y.-Z. Hu, C. Chamchoumis, J.S. Grebowicz, R.P. Thummel, Inorg. Chem. 41, 2296 (2002)

    Article  CAS  Google Scholar 

  26. T. Kawano, J. Kuwana, I. Ueda, Bull. Chem. Soc. Jpn. 76, 789 (2003)

    Article  CAS  Google Scholar 

  27. E. Bosch, C.L. Barnes, N.L. Brennan, G.L. Eakins, B.E. Breyfogle, J. Org. Chem. 73, 3931 (2008)

    Article  CAS  Google Scholar 

  28. L. Kaganovsky, K.-B. Cho, D. Gelman, Organometallics 27, 5139 (2008)

    Article  CAS  Google Scholar 

  29. P. Štěpniěka, M. Krupa, M. Lamač, I. Císařová, J. Organomet. Chem. 694, 2987 (2009)

    Article  Google Scholar 

  30. A. Gillie, J.K. Stille, J. Am. Chem. Soc. 102, 4933 (1980)

    Article  CAS  Google Scholar 

  31. S. Shotwell, H.L. Ricks, J.G.M. Morton, M. Laskoski, J. Fiscus, M.D. Smith, K.D. Shimizu, H.-C. zur Loye, U.H.F. Bunz, J. Organomet. Chem. 671, 43 (2003)

    Article  CAS  Google Scholar 

  32. R.C. Larock, E.K. Yum, M.D. Refvik, J. Org. Chem. 63, 7652 (1998)

    Article  CAS  Google Scholar 

  33. E.V. Tretyakov, D.W. Knight, S.F. Vasilevsky, J. Chem. Soc. Perkin Trans. 1, 3713 (1999)

    Article  Google Scholar 

  34. J.M. Keith, R.J. Nielsen, J. Oxgaard, W.A. Goddard III, J. Am. Chem. Soc. 127, 13172 (2005)

    Article  CAS  Google Scholar 

  35. A. Ricci, F. Angelucci, M. Bassetti, C.L. Sterzo, J. Am. Chem. Soc. 124, 1060 (2002)

    Article  CAS  Google Scholar 

  36. A.L. Casado, P. Espinet, Organometallics 17, 954 (1998)

    Article  CAS  Google Scholar 

  37. J.M. Keith, W.A. Goddard III, J. Am. Chem. Soc. 131, 1416 (2009)

    Article  CAS  Google Scholar 

  38. C. Amatore, A. Jutand, A. Suarez, J. Am. Chem. Soc. 115, 9531 (1993)

    Article  CAS  Google Scholar 

  39. F. Kessler, B. Weibert, H. Fischer, Organometallics 29, 5154 (2010)

    Article  CAS  Google Scholar 

  40. K. Osakada, R. Sakata, T. Yamamoto, Organometallics 16, 5354 (1997)

    Article  CAS  Google Scholar 

  41. X. Li, T. Vogel, C.D. Incarvito, R.H. Crabtree, Organometallics 24, 62 (2005)

    Article  Google Scholar 

  42. B.M. Trost, Chem. Eur. J. 4, 2405 (1998)

    Article  CAS  Google Scholar 

  43. H. Makabe, E.-I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, vol. 2 (Wiley, New York, 2002), p. 2789

    Book  Google Scholar 

  44. N. Sakai, R. Komatsu, N. Uchiba, R. Ikeda, T. Konakahara, Org. Lett. 12, 1300 (2010)

    Article  CAS  Google Scholar 

  45. A. Rosiak, W. Fery, J. Christoffers, Eur. J. Org. Chem. 4044 (2006)

  46. P.D. Woodgate, S.H. Sutherland, J. Organomet. Chem. 629, 131 (2001)

    Article  CAS  Google Scholar 

  47. M. Beshai, B. Dhudshia, R. Mills, A.N. Thadani, Tetrahedron Lett. 49, 6794 (2008)

    Article  CAS  Google Scholar 

  48. C.-F. Lin, Y.-H. Lo, M.-C. Hsieh, Y.-H. Chen, J.-J. Wang, M.-J. Wu, Bioorg. Med. Chem. 13, 3565 (2005)

    Article  CAS  Google Scholar 

  49. K.-F. Tseng, C.-F. Lin, Y.-H. Lo, Y.-L. Hu, L.-Y. Chen, S.-H. Yang, S.-R. Lin, L.-S. Chang, M.-J. Wu, Eur. J. Med. Chem. 44, 35 (2009)

    Article  CAS  Google Scholar 

  50. T. Kawano, T. Shinomaru, I. Ueda, Org. Lett. 4, 2545 (2002)

    Article  CAS  Google Scholar 

  51. J.-H. Li, Y. Liang, Y.-X. Xie, J. Org. Chem. 70, 4393 (2005)

    Article  CAS  Google Scholar 

  52. K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 47, 2407 (2008)

    Article  CAS  Google Scholar 

  53. Z. Chen, H. Jiang, A. Wang, S. Yang, J. Org. Chem. 75, 6700 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported in part by the Grant-in-Aid for Young Scientists (B) from The Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan (no. 19750082), and by a Shionogi Pharmaceuticals Inc. Award in Synthetic Organic Chemistry, Japan, through The Society of Synthetic Organic Chemistry, Japan, granted to M.S.

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka, 599-8531, Japan

    Shingo Atobe, Motohiro Sonoda, Yuki Suzuki, Takuya Yamamoto, Haruna Masuno, Hiroyuki Shinohara & Akiya Ogawa

Authors
  1. Shingo Atobe
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Motohiro Sonoda
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yuki Suzuki
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Takuya Yamamoto
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Haruna Masuno
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hiroyuki Shinohara
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Akiya Ogawa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Motohiro Sonoda.

Additional information

This article is published as part of a themed issue in honor of Professor Kazuhiko Mizuno’s research accomplishments on the occasion of his retirement.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Atobe, S., Sonoda, M., Suzuki, Y. et al. Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene. Res Chem Intermed 39, 359–370 (2013). https://doi.org/10.1007/s11164-012-0654-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0654-2

Keywords

Search

Navigation