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.

  • Comment
  • Published:

Celebrating 100 years of the Rosenmund reaction

This year marks a century since the pioneering work leading to what is now known as the Rosenmund reduction. We celebrate this landmark, reflecting upon the evolution of synthetic methodologies for reductive aldehyde synthesis from carboxylic acid derivatives and highlighting modern, improved strategies.

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: Classic strategies for synthesis of aldehydes from carboxylic acids.
Fig. 2: Overview of aldehyde reductive synthesis.
Fig. 3: Modern applications of the Rosenmund reduction.

References

  1. Mazzeo, T. J. The Secret of Chanel No. 5: The Intimate History of the World's Most Famous Perfume (HarperCollins, New York, 2010).

    Google Scholar 

  2. Franke, R., Selent, D. & Börner, A. Chem. Rev. 112, 5675–5732 (2012).

    Article  CAS  PubMed  Google Scholar 

  3. Bäckvall, J.-E. Modern Oxidation Methods. 2nd edn (Wiley, Weinheim, 2010).

    Book  Google Scholar 

  4. Magano, J. & Dunetz, J. R. Org. Process Res. Dev. 16, 1156–1184 (2012).

    Article  CAS  Google Scholar 

  5. Rosenmund, K. W. Chem. Ber. 51, 585–593 (1918).

    Article  CAS  Google Scholar 

  6. Rosenmund, K. W. & Zetzsche, F. Chem. Ber. 54, 425–437 (1921).

    Article  Google Scholar 

  7. Crawford, J. B. et al. Org. Process Res. Dev. 12, 823–830 (2008).

    Article  CAS  Google Scholar 

  8. Britton, H. et al. Org. Process Res. Dev. 16, 1607–1617 (2012).

    Article  CAS  Google Scholar 

  9. Muraki, M. & Mukaiyama, T. Chem. Lett. 3, 1447–1450 (1974).

    Article  Google Scholar 

  10. Brown, H. C., Cha, J. S., Nazer, B. & Yoon, N. M. J. Am. Chem. Soc. 106, 8001–8002 (1984).

    Article  CAS  Google Scholar 

  11. Brown, H. C. & Ramachandran, P. V. in Reductions in Organic Synthesis (ed. Abdel-Magid, A. F.) 1–30 (ACS Symposium Series, American Chemical Society, Washington DC, 1996).

  12. Fukuyama, T., Lin, S.-C. & Li, L. J. Am. Chem. Soc. 112, 7050–7051 (1990).

    Article  CAS  Google Scholar 

  13. Nagayama, K., Shimizu, I. & Yamamoto, A. Bull. Chem. Soc. Jpn 74, 1803–1815 (2001).

    Article  CAS  Google Scholar 

  14. Gooßen, L. K., Khan, B. A., Fett, T. & Treu, M. Adv. Synth. Catal. 352, 2166–2170 (2010).

    Article  CAS  Google Scholar 

  15. Gooßen, L. K. & Ghosh, K. Chem. Commun. 836–837 (2002).

  16. Fujihara, T., Cong, C., Terao, J. & Tsuji, Y. Adv. Synth. Catal. 335, 3420–3424 (2013).

    Article  CAS  Google Scholar 

  17. Parks, D. J. & Piers, W. E. J. Am. Chem. Soc. 118, 9440–9441 (1996).

    Article  CAS  Google Scholar 

  18. Cheng, C. & Brookhart, M. Angew. Chem. Int. Ed. 51, 9422–9424 (2012).

    Article  CAS  Google Scholar 

  19. Miyamoto, K., Motoyama, Y. & Nagashima, H. Chem. Lett. 41, 229–231 (2012).

    Article  CAS  Google Scholar 

  20. Misal Castro, L. C., Li, H., Sortais, J.-B. & Darcel, C. Chem. Commun. 48, 10514–10516 (2012).

    Article  CAS  Google Scholar 

  21. Li, H. et al. Angew. Chem. Int. Ed. 52, 8045–8049 (2013).

    Article  CAS  Google Scholar 

  22. Zheng, J., Chevance, S., Darcel, C. & Sortais, J.-B. Chem. Commun. 49, 10010–10012 (2013).

    Article  CAS  Google Scholar 

  23. Bézier, D., Park, S. & Brookhart, M. Org. Lett. 15, 496–499 (2013).

    Article  CAS  PubMed  Google Scholar 

  24. Spletstoser, J. T., White, J. M., Tunoori, A. R. & Georg, G. I. J. Am. Chem. Soc. 129, 3408–3419 (2007).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Pelletier, G., Bechara, W. S. & Charette, A. B. J. Am. Chem. Soc. 132, 12817–12819 (2010).

    Article  CAS  PubMed  Google Scholar 

  26. Tinnis, F., Volkov, A., Slagbrand, T. & Adolfsson, H. Angew. Chem. Int. Ed. 52, 4562–4566 (2016).

    Article  CAS  Google Scholar 

  27. Zhang, M. et al. Chem. Commun. 53, 10228–10231 (2017).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Joakim Bergman.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Iosub, A.V., Wallentin, CJ. & Bergman, J. Celebrating 100 years of the Rosenmund reaction. Nat Catal 1, 645–648 (2018). https://doi.org/10.1038/s41929-018-0143-0

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41929-018-0143-0

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