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ORGANOBISMUTH CHEMISTRY

Heavy metal orchestration

Many current methods to prepare 2-hydroxybiaryls require the prefunctionalization of phenol groups or show limited substrate scope. Now, use of a pentavalent sulfone-bridged bismacycle, formed in situ by telescoped boron-to-bismuth transmetallation and oxidation, allows the direct and regioselective ortho-arylation of unprotected phenols.

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Fig. 1: Development of a general method for the direct and regioselective ortho-arylation of unprotected phenols via a telescoped one-pot boron-to-bismuth transmetallation and oxidation sequence.

References

  1. 1.

    Cramer, J., Sager, C. P. & Ernst, B. J. Med. Chem. 62, 8915–8930 (2019).

    CAS  Article  Google Scholar 

  2. 2.

    Roughley, S. D. & Jordan, A. M. J. Med. Chem. 54, 3451–3479 (2011).

    CAS  Article  Google Scholar 

  3. 3.

    McGrath, N. A., Brichacek, M. & Njardarson, J. T. J. Chem. Educ. 87, 1348–1349 (2010).

    CAS  Article  Google Scholar 

  4. 4.

    Brown, D. G. & Boström, J. J. Med. Chem. 59, 4443–4458 (2016).

    CAS  Article  Google Scholar 

  5. 5.

    Quideau, S., Deffieux, D., Douat-Casassus, C. & Pouységu, L. Angew. Chem. Int. Ed. 50, 586–621 (2011).

    CAS  Article  Google Scholar 

  6. 6.

    Hassan, J., Sévignon, M., Gozzi, C., Schulz, E. & Lemaire, M. Chem. Rev. 102, 1359–1469 (2002).

    CAS  Article  Google Scholar 

  7. 7.

    Huang, Z. & Lumb, J.-P. ACS Catal. 9, 521–555 (2019).

    CAS  Article  Google Scholar 

  8. 8.

    Jurrat, M., Maggi, L., Lewis, W. & Ball, L. T. Nat. Chem. https://doi.org/10.1038/s41557-020-0425-4 (2020).

  9. 9.

    Gagnon, A., Dansereau, J. & Le Roch, A. Synthesis 49, 1707–1745 (2017).

    CAS  Article  Google Scholar 

  10. 10.

    Gagnon, A., Benoit, E. & Le Roch, A. in Science of Synthesis Knowledge Updates Vol. 4, 1–111 (Thieme, 2018).

  11. 11.

    Barton, D. H. R., Lester, D. J., Motherwell, W. B. & Barros Papoula, M. T. J. Chem. Soc. Chem. Commun. 246–247 (1980).

  12. 12.

    Suzuki, H., Murafuji, T. & Azuma, N. J. Chem. Soc. Perkin Trans. I 1593–1600 (1992).

Download references

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Correspondence to Alexandre Gagnon.

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Le Roch, A., Gagnon, A. Heavy metal orchestration. Nat. Chem. 12, 223–224 (2020). https://doi.org/10.1038/s41557-020-0434-3

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