Skip to main content
SpringerLink
Log in

Microwave-assisted, Ir-catalyzed aromatic C–H borylation

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

Abstract

One-step conversions of 1,3-disubstituted benzenes to aryl boronates and 2,6-disubstituted pyridines to heteroaryl boronates are described. Microwave heating was used for all reactions. [(COD)Ir(μ-OMe)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine were used as catalysts, in methyl tert-butyl ether. Acceleration of the rate of reaction was remarkable compared with that of same reaction under conventional heating conditions.

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

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457 (1995)

    Article  CAS  Google Scholar 

  2. D.M.T. Chan, K.L. Monaco, R. Li, D. Bonne, C.G. Clarke, P.Y.S. Lam, Tetrahedron Lett. 44, 3863 (2003)

    Article  CAS  Google Scholar 

  3. M.P. Sibi, H. Tatamidani, K. Patil, Org. Lett. 7, 2571 (2005)

    Article  CAS  Google Scholar 

  4. G. Chen, N. Tokunaga, T. Hayashi, Org. Lett. 7, 2881 (2005)

    Article  Google Scholar 

  5. T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 60, 7508–7510 (1995)

    Article  CAS  Google Scholar 

  6. H. Chen, J.F. Hartwig, Angew. Chem. Int. Ed. 38, 3391 (1999)

    Article  CAS  Google Scholar 

  7. H. Chen, S. Schlecht, T.C. Semple, J.F. Hartwig, Science 287, 1995 (2000)

    Article  CAS  Google Scholar 

  8. M.K. Tse, J.-Y. Cho, M.R. Smith III, Org. Lett. 3, 2831 (2001)

    Article  CAS  Google Scholar 

  9. J.-Y. Cho, C.N. Iverson, M.R. Smith III, J. Am. Chem. Soc. 122, 12868 (2000)

    Article  CAS  Google Scholar 

  10. T. Ishiyama, N. Miyaura, J. Org. Chem. 680, 3 (2003)

    Article  CAS  Google Scholar 

  11. H. Tamura, H. Yamazaki, H. Sato, S. Sakaki, J. Am. Chem. Soc. 125, 16114 (2003)

    Article  CAS  Google Scholar 

  12. F. Shi, M.R. Smith III, R.E. Maleczka Jr, Org. Lett. 8, 1411–1414 (2006)

    Article  CAS  Google Scholar 

  13. J.M. Murphy, C.C. Tzschucke, J.F. Hartwig, Org. Lett. 9, 757–760 (2007)

    Article  CAS  Google Scholar 

  14. D. Holmes, G.A. Chotana, R.E. Maleczka Jr, M.R. Smith III, Org. Lett. 8, 1407–1410 (2006)

    Article  CAS  Google Scholar 

  15. J.M. Murphy, X. Liao, J.F. Hartwig, J. Am. Chem. Soc. 129, 15434 (2007)

    Article  CAS  Google Scholar 

  16. R.E. Maleczka Jr, F. Shi, D. Holmes, M.R. Smith III, J. Am. Chem. Soc. 125, 2003 (2002)

    Google Scholar 

  17. C.O. Kappe, Angew. Chem. Int. Ed. 43, 6250–6284 (2004)

    Article  CAS  Google Scholar 

  18. H. Tamura, H. Yamazaki, H. Sato, S. Sakaki, J. Am. Chem. Soc. 125, 16115 (2003)

    Google Scholar 

  19. T.A. Boebel, J.F. Hartwig, Tetrahedron 64, 6824–6830 (2008)

    Article  CAS  Google Scholar 

  20. P. Harrisson, J. Morris, P.G. Steel, T.B. Marder, Synlett 1, 147 (2009)

    Google Scholar 

  21. T. Ishiyama, J. Takagi, J.F. Hartwig, N. Miyaura, Angew. Chem. 41, 3056 (2002)

    Article  CAS  Google Scholar 

  22. P. Harrisson, J. Morris, T.B. Marder, P.G. Steel, Org. Lett. 11, 3586–3589 (2009)

    Article  CAS  Google Scholar 

  23. T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N.R. Anastasi, J.F. Hartwig, J. Am. Chem. Soc. 124, 390 (2002)

    Article  CAS  Google Scholar 

  24. T. Ishiyama, N. Miyaura, Pure Appl. Chem. 78, 1369–1375 (2006)

    Article  CAS  Google Scholar 

  25. T. Ishiyama, N. Miyaura, J. Org. Chem. 680, 7 (2003)

    Google Scholar 

Download references

Acknowledgments

The authors acknowledge the generous support of this study by Sundia MediTech Company Ltd.

Author information

Authors and Affiliations

  1. College of Pharmacy, Institute of New Drug Research, Jinan University, Guangzhou, 510632, China

    Li Zeqing, Liang Zhibin, Wang Yuqiang & Yu Pei

  2. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drug Research, Guangzhou, 510632, China

    Wang Yuqiang & Yu Pei

Authors
  1. Li Zeqing
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Liang Zhibin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wang Yuqiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu Pei
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu Pei.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zeqing, L., Zhibin, L., Yuqiang, W. et al. Microwave-assisted, Ir-catalyzed aromatic C–H borylation. Res Chem Intermed 39, 1917–1926 (2013). https://doi.org/10.1007/s11164-012-0725-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0725-4

Keyword

Search

Navigation