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:

Photochemistry

Diradical ring formation

Lactams and pyridines are privileged scaffolds, but strategies for combining these groups into one molecule are lacking. Now, N–N pyridinium ylides have been shown to form triplet state diradicals under photoinduced energy transfer, and subsequent [3+2] cycloaddition with the tethered alkene enables the synthesis of diverse ortho-pyridyl lactams.

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

Access options

Buy this article

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

Fig. 1: Discovery of energy-transfer-induced [3+2] photocycloaddition for N-heterocycle synthesis.

References

  1. Vitaku, E., Smith, D. T. & Njardarson, J. T. J. Med. Chem. 57, 10257–10274 (2014).

    Article  CAS  PubMed  Google Scholar 

  2. Caruano, J., Muccioli, G. G. & Robiette, R. Org. Biomol. Chem. 14, 10134–10156 (2016).

    Article  CAS  PubMed  Google Scholar 

  3. Ling, Y. et al. Drug Des. Devel. Ther. 15, 4289–4338 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Wang, P., Zhao, Q., Xiao, W. & Chen, J. Green Synth. Catal. 1, 42–51 (2020).

    Article  Google Scholar 

  5. Harmata, A. S., Roldan, B. J. & Stephenson, C. R. J. Angew. Chem. Int. Ed. 62, e202213003 (2023).

    Article  CAS  Google Scholar 

  6. Bera, M., Lee, D. S. & Cho, E. J. Trends Chem. 3, 877–891 (2021).

    Article  CAS  Google Scholar 

  7. Lee, W., Koo, Y., Jung, H., Chang, S. & Hong, S. Nat. Chem. https://doi.org/10.1038/s41557-023-01258-2 (2023).

    Article  PubMed  Google Scholar 

  8. Strieth-Kalthoff, F. & Glorius, F. Chem 6, 1888–1903 (2020).

    Article  CAS  Google Scholar 

  9. Wang, M.-M., Nguyen, T. V. T. & Waser, J. Chem. Soc. Rev. 51, 7344–7357 (2022).

    Article  CAS  PubMed  Google Scholar 

  10. Yin, Y., Zhao, X. & Jiang, Z. Chin. J. Org. Chem. 42, 1609–1625 (2022).

    Article  CAS  Google Scholar 

  11. Genzink, M. J., Kidd, J. B., Swords, W. B. & Yoon, T. P. Chem. Rev. 122, 1654–1716 (2022).

    Article  CAS  PubMed  Google Scholar 

  12. Poplata, S., Tröster, A., Zou, Y.-Q. & Bach, T. Chem. Rev. 116, 9748–9815 (2016).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jia-Rong Chen.

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

Wang, PZ., Chen, JR. Diradical ring formation. Nat. Chem. 15, 1058–1059 (2023). https://doi.org/10.1038/s41557-023-01263-5

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41557-023-01263-5

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