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.

ORGANOMETALLIC CHEMISTRY

Strained boronates do the trick

Strained boronate complexes have now been shown to enable an unprecedented cross-coupling reaction across a C–C σ-bond. Using this approach, highly functionalized cyclobutanes can be prepared with excellent stereocontrol from readily available reagents.

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

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

Fig. 1: Comparison between the conjunctive cross-coupling as described by Morken and the carbopalladation of strained σ-bonds as reported by Aggarwal.

References

  1. De Meijere, A., Bräse, S. & Oestreich, M. (eds) Metal Catalyzed Cross-Coupling Reactions and More (Wiley, London, 2013).

  2. Miyaura, N. & Suzuki, A. Chem. Rev. 95, 2457–2483 (1995).

    Article  CAS  Google Scholar 

  3. Mangano, J. & Dunetz, J. R. Chem. Rev. 111, 2177–2250 (2011).

    Article  Google Scholar 

  4. Lennox, A. J. J. & Lloyd-Jones, G. C. Chem. Soc. Rev. 43, 412–443 (2014).

    Article  CAS  Google Scholar 

  5. Zhang, L. et al. Science 351, 70–74 (2016).

    Article  CAS  Google Scholar 

  6. Fawcett, A., Biberger, T. & Aggarwal, V. K. Nat. Chem. https://doi.org/10.1038/s41557-018-0181-x (2018).

    Article  PubMed  Google Scholar 

  7. Walczak, M. A. A., Krainz, T. & Wipf, P. Acc. Chem. Res. 48, 1149–1158 (2015).

    Article  CAS  Google Scholar 

  8. Taylor, R. D., MacCoss, M. & Lawson, A. D. G. J. Med. Chem. 57, 5845–5859 (2014).

    Article  CAS  Google Scholar 

  9. Lovering, F., Bikker, J. & Humblet, C. J. Med. Chem. 52, 6752–6756 (2009).

    Article  CAS  Google Scholar 

  10. Sandford, C. & Aggarwal, V. K. Chem. Commun. 53, 5481–5494 (2017).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mariola Tortosa.

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Parra, A., Tortosa, M. Strained boronates do the trick. Nature Chem 11, 104–106 (2019). https://doi.org/10.1038/s41557-018-0202-9

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41557-018-0202-9

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