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:

C–H carbonylation

In situ acyl triflates ace it

A simple palladium catalyst has mediated the facile formation of aroyl triflates — an extremely reactive class of electrophiles. These intermediates, generated in situ, enable the Friedel–Crafts acylation of traditionally unreactive arenes, addressing a significant gap in C–H carbonylation methodology.

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

Figure 1: Comparison between different strategies to access acyl triflates and synthetic applicability of the reaction developed by Arndtsen and co-workers1.

References

  1. Kinney, R. G. et al. Nat. Chem. 10, 193–199 (2018).

    Article  Google Scholar 

  2. Olah, G. A. Friedel-Crafts Chemistry (Wiley-Interscience, 1973).

  3. Effenberger, F. & Epple, G. Angew. Chem. Int. Ed. 11, 299–300 (1972).

    Article  CAS  Google Scholar 

  4. Effenberger, F., Epple, G., Eberhard, J. K., Bühler, U. & Sohn, E. Chem. Ber. 116, 1183–1194 (1983).

    Article  CAS  Google Scholar 

  5. Wu, X.-F., Neumann, H. & Beller, M. Chem. Soc. Rev. 40, 4986–5009 (2011).

    Article  CAS  Google Scholar 

  6. Petrone, D. A., Ye, J. & Lautens, M. Chem. Rev. 116, 8003–8104 (2016).

    Article  CAS  Google Scholar 

  7. Quesnel, J. S. & Arndtsen, B. A. J. Am. Chem. Soc. 135, 16841–16844 (2013).

    Article  CAS  Google Scholar 

  8. Fang, X., Cacherat, B. & Morandi, B. Nat. Chem. 9, 1105–1109 (2017).

    Article  CAS  Google Scholar 

  9. Roy, A. H. & Hartwig, J. F. J. Am. Chem. Soc. 125, 13944–13945 (2003).

    Article  CAS  Google Scholar 

  10. Shen, X., Hyde, A. M. & Buchwald, S. L. J. Am. Chem. Soc. 132, 14076–14078 (2010).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Bill Morandi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lee, Y., Morandi, B. In situ acyl triflates ace it. Nature Chem 10, 116–117 (2018). https://doi.org/10.1038/nchem.2934

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/nchem.2934

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