Skip to main content
SpringerLink
Log in

Novel palladium-catalyzed domino reaction of 2-methylindoles with 2-iodobenzyl bromide

  • LETTERS TO THE EDITOR
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A novel palladium-catalyzed domino reaction of 2-methylindoles with 2-iodobenzyl bromide in the system Pd(OAc)2/Xantphos/t-BuOK/PhMe leading to indole-fused tricyclo[7,3,1,02,7]trideca-2(7),3,5-triene ring system is presented. Pd-catalyzed reaction of 2-methylindole with 5-bromo-6-bromomethylbenzo[1, 3]dioxole afforded 3,3-bis(6-bromobenzo[1, 3]dioxol-5-ylmethyl)-2-methyl-3H-indole.

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

Figure 1

Similar content being viewed by others

References

  1. (a) Chadwick, T. In Comprehensive Heterocyclic Chemistry I; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, vol. 4, p. 155. (b) Jones, G. B.; Chapman, B. J. In Comprehensive Comprehensive Heterocyclic Chemistry II; Katritzky, A. R; Rees, C. W.; Scriven, E. F. V.; Eds.; Pergamon: Oxford, 1996, Vol. 2, p. 1. (c) Black, D. S. C. In Comprehensive Heterocyclic Chemistry II, Katritzky, A. R; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, Vol. 2, p. 40.

  2. (a) Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, Vol. 2, p. 207. (b) d'Ischia, M.; Neopolitano, A.; Pezzella, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Vol. 3, p. 1. (c) Trofimov, B. A.; Nedolya, N. A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Vol. 3, p. 45. (d) Bergman, J.; Janosik, T. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Vol. 3, p. 269.

  3. (a) Sunberg, R. Indoles; Academic Press: London, 1996. (b) Remers, W. E. In Indoles, Part 1; Houlihan, W. J., Ed.; John Wiley & Sons: New York, 1983, p. 1.

  4. Rodriguez, J. G.; Urrutia, A. J. Heterocycl. Chem. 1999, 36, 129.

    Article  CAS  Google Scholar 

  5. Chen, J.; Cook, M. J. Org. Lett. 2013, 15, 1088.

    Article  Google Scholar 

  6. Fisher, E.; Steche, A. Justus Liebigs Ann. Chem. 1887, 242, 348.

    Article  Google Scholar 

  7. Hoshino, T. Justus Liebigs Ann. Chem. 1933, 500, 35.

    Article  Google Scholar 

  8. Kandukari, S. R.; Schiffner, J. A.; Oestreich, H. Angew. Chem., Int Ed. 2012, 51, 1266.

  9. Wu, K.-J.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 3772.

    Article  CAS  Google Scholar 

  10. Montgomery, T. D.; Zhu, Y.; Kogan, N., Rawal, V. H. Org. Lett. 2013, 15, 1140.

    Article  CAS  Google Scholar 

  11. Cai, Q.; Zhen, C.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 8666.

  12. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.

    Google Scholar 

  13. Mackay, S.; Dong, W.; Edwards, C.; Henderson, A.; Gilmore, C. J.; Stewart, N.; Shankland, K.; Donald, A. maXus, Integrated Crystallography Software; Bruker-Nonius and University of Glasgow, 2003.

Download references

Author information

Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    Edgars Abele, Sergey Belyakov, Tatyana Beresneva, Lena Golomba & Ramona Abele

Authors
  1. Edgars Abele
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sergey Belyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tatyana Beresneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lena Golomba
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ramona Abele
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Edgars Abele.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(2), 140–142

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Abele, E., Belyakov, S., Beresneva, T. et al. Novel palladium-catalyzed domino reaction of 2-methylindoles with 2-iodobenzyl bromide. Chem Heterocycl Comp 52, 140–142 (2016). https://doi.org/10.1007/s10593-016-1846-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1846-2

Keywords

Search

Navigation