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.

Organic synthesis

New uses for old building blocks

Nature Chemistry volume 1, pages 433–434 (2009)Cite this article

New methodology that couples together carbonyl compounds with boronic acids shows much promise for synthesis owing to ease of access of the building blocks, functional group tolerance and broad scope of the reaction.

In general, the two ends of the molecular building blocks have to be activated in some way to make them 'sticky' before they can be joined together. Furthermore, the activation process has to be selective for a specific site, which becomes increasingly difficult for increasingly complex molecules. Thus, methods that combine readily available building blocks under mild conditions are very important to the continued development of organic synthesis. Writing on page 494 of this issue, Barluenga, Valdés and co-workers now report a remarkably simple method for combining aldehydes or ketones with boronic esters — three widely available classes of building blocks — that can be used to make C–C bonds1.

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

Access options

Rent or buy this article

Get just this article for as long as you need it

$39.95

Learn more

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

Figure 1: Construction of complex chemical compounds from simple building blocks.
Figure 2: Successful and unsuccessful reactions of diazoesters with boron derivatives.

References

  1. Barluenga, J., Tomás-Gamasa, M., Aznar, F. & Valdés, C. Nature Chem. 1, 494–499 10/1038/nchem.328(2009).

    Article  CAS  Google Scholar 

  2. Hooz, J. & Linke, S. J. Am. Chem. Soc. 90, 5936–5937 (1968).

    Article  CAS  Google Scholar 

  3. Brown, H. C., Midland, M. M. & Levy, A. B. J. Am. Chem. Soc. 94, 3662–3664 (1972).

    Article  CAS  Google Scholar 

  4. Peng, C., Zhang, W., Yan, G. & Wang, J. Org. Lett. 11, 1667–1670 (2009).

    Article  CAS  Google Scholar 

  5. Closs, G. L. & Moss, R. A. J. Am. Chem. Soc. 86, 4042–4053 (1964).

    Article  CAS  Google Scholar 

  6. Fulton, J. R., Aggarwal, V. K. & de Vicente, J. Eur. J. Org. Chem. 1479–1492 (2005).

Download references

Author information

Authors and Affiliations

  1. Varinder K. Aggarwal is in the School of Chemistry, University of Bristol, Cantock's Close, Bristol BS1 1TS, UK. v.aggarwal@bristol.ac.uk,

    Varinder K. Aggarwal

Authors
  1. Varinder K. Aggarwal
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Aggarwal, V. New uses for old building blocks. Nature Chem 1, 433–434 (2009). https://doi.org/10.1038/nchem.346

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/nchem.346

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