Skip to main content

Iron-Catalyzed Phenanthrene Synthesis from Alkyne and Aryl Bromide Mediated by Metallic Magnesium

  • Chapter
  • First Online:
Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H Bond Activation

Part of the book series: Springer Theses ((Springer Theses))

  • 422 Accesses

Abstract

In the previous two chapters, iron-catalyzed synthesis of fused aromatics via C–H bond activation was developed. Although the reaction proceeds under mild conditions, the use of an unstable Grignard reagent is a practical disadvantage from the viewpoint of synthetic chemistry. Therefore, the reaction using an aryl bromide under reductive conditions instead of using Grignard reagents was envisioned to develop more practical iron-catalyzed reactions.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Bogdanovic, B., & Schwickardi, M. (2000). Angewandte Chemie, 112, 4788–4790.

    Article  Google Scholar 

  2. Bogdanovic, B., & Schwickardi, M. (2000). Angewandte Chemie International Edition, 39, 4610–4612.

    Article  CAS  Google Scholar 

  3. Czaplik, W. M., Mayer, M., & Wangelin, A. J. (2009). Angewandte Chemie, 121, 616–620.

    Article  Google Scholar 

  4. Czaplik, W. M., Mayer, M., & Wangelin, A. J. (2009). Angewandte Chemie International Edition, 48, 607–610.

    Article  CAS  Google Scholar 

  5. Czaplik, W. M., Mayer, M., & Wangelin, A. J. (2011). ChemCatChem, 3, 135–138.

    Article  CAS  Google Scholar 

  6. Norinder, J., Matsumoto, A., Yoshikai, N., & Nakamura, E. (2008). Journal of the American Chemical Society, 130, 5858–5859.

    Article  CAS  Google Scholar 

  7. Yoshikai, N., Matsumoto, A., Norinder, J., & Nakamura, E. (2009). Angewandte Chemie International Edition, 48, 2925–2928.

    Article  CAS  Google Scholar 

  8. Yoshikai, N., Matsumoto, A., Norinder, J., & Nakamura, E. (2010) Synlett, 313–316.

    Google Scholar 

  9. Ilies, L., Asako, S., & Nakamura, E. (2011). Journal of the American Chemical Society, 133, 7672–7675.

    Article  CAS  Google Scholar 

  10. Yoshikai, N., Asako, S., Yamakawa, T., Ilies, L., & Nakamura, E. (2011). Chemistry an Asian Journal 6, 3059–3065.

    Google Scholar 

  11. Ilies, L., Motoaki, K., Matsumoto, A., Yoshikai, N., & Nakamura, E. (2012). Advanced Synthesis and Catalysis 354, 593–596.

    Google Scholar 

  12. Wu, G., Rheingold, A. L., Geib, S. J., & Heck, R. F. (1987). Organometallics, 6, 1941–1946.

    Article  CAS  Google Scholar 

  13. Larock, R. C., Doty, M. J., Tian, Q., & Zenner, J. M. (1997). Journal of Organic Chemistry, 62, 7536–7537.

    Article  CAS  Google Scholar 

  14. Still, W. C., Kahn, M., & Mitra, A. (1978). Journal of Organic Chemistry, 43, 2923–2924.

    Article  CAS  Google Scholar 

  15. Pangborn, A. B., Giardello, M. A., Grubbs, R. H., Rosen, R. K., & Timmers, F. J. (1996). Organometallics, 15, 1518–1520.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Arimasa Matsumoto .

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer Japan

About this chapter

Cite this chapter

Matsumoto, A. (2014). Iron-Catalyzed Phenanthrene Synthesis from Alkyne and Aryl Bromide Mediated by Metallic Magnesium. In: Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H Bond Activation. Springer Theses. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54928-4_4

Download citation

Publish with us

Policies and ethics