Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • News & Views
  • Published:

Synthetic methodology

Ring expansion and chain extension of alkyl amines

Nature Chemistry volume 17, pages 1299–1300 (2025)Cite this article

Subjects

Amines are highly valued molecules, used to understand biological processes and in the discovery of new medicines. However, medium-sized cyclic and macrocyclic amines are extremely challenging to synthesize and are therefore underutilized. Now, up to 15-membered cyclic amines can be formed directly from smaller, more accessible rings via an organoborane-catalysed two-carbon-unit C–C bond insertion.

This is a preview of subscription content, access via your institution

Access options

Rent or buy this article

Prices vary by article type

from$1.95

to$39.95

Learn more

Prices may be subject to local taxes which are calculated during checkout

Fig. 1: Organoborane-catalysed ring expansion and chain elongation of tertiary alkyl amines.

References

  1. Marshall, C. M. et al. J. Med. Chem. 67, 11622–11655 (2024).

    Article  CAS  PubMed  Google Scholar 

  2. Jimenez, D. G. et al. J. Med. Chem. 66, 5377–5396 (2023).

    Article  Google Scholar 

  3. Gradillas, A. & Pérez-Castells, J. Angew. Chem. Int. Edn 45, 6086–6101 (2006).

    Article  CAS  Google Scholar 

  4. Mortensen, K. T. et al. Chem. Rev. 119, 10288–10317 (2019).

    Article  CAS  PubMed  Google Scholar 

  5. Donald, J. R. & Unsworth, W. P. Chem. Eur. J. 23, 8780–8799 (2017).

    Article  CAS  PubMed  Google Scholar 

  6. Zhou, X.-Y., Liu, L., Lyu, H. & Wang, X.-C. Nat. Chem. https://doi.org/10.1038/s41557-025-01849-1 (2025).

    Article  PubMed  PubMed Central  Google Scholar 

  7. Basak, S. et al. Chem. Soc. Rev. 50, 3720–3737 (2021).

    Article  CAS  PubMed  Google Scholar 

  8. Gillions, J. P. et al. Synlett 34, 2117–2128 (2023).

    Article  CAS  Google Scholar 

  9. Dai, C. et al. Asian J. Org. Chem. 12, e202300198 (2023).

    Article  CAS  Google Scholar 

  10. Jones, B. T. & Maulide, N. Angew. Chem. Int. Edn 63, e202320001 (2024).

    Article  CAS  Google Scholar 

  11. Zhou, X.-Y. et al. ACS Catal. 14, 8041–8049 (2024).

    Article  CAS  Google Scholar 

  12. Zhang, M. et al. Angew. Chem. Int. Edn 63, e202317610 (2024).

    Article  CAS  Google Scholar 

  13. Alvarez-Montoya, A. et al. ACS Catal. 14, 4856–4864 (2024).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Efimov, I. V. et al. Eur. J. Org. Chem. 26, e202201450 (2023).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry, University of Leicester, Leicester, UK

    Maryia Barysevich & Alexander P. Pulis

Authors
  1. Maryia Barysevich
    View author publications

    Search author on:PubMed Google Scholar

  2. Alexander P. Pulis
    View author publications

    Search author on:PubMed Google Scholar

Corresponding author

Correspondence to Alexander P. Pulis.

Ethics declarations

Competing interests

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Barysevich, M., Pulis, A.P. Ring expansion and chain extension of alkyl amines. Nat. Chem. 17, 1299–1300 (2025). https://doi.org/10.1038/s41557-025-01920-x

Download citation

  • Published:

  • Version of record:

  • Issue date:

  • DOI: https://doi.org/10.1038/s41557-025-01920-x

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing