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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References
Cramer, J., Sager, C. P. & Ernst, B. J. Med. Chem. 62, 8915–8930 (2019).
Roughley, S. D. & Jordan, A. M. J. Med. Chem. 54, 3451–3479 (2011).
McGrath, N. A., Brichacek, M. & Njardarson, J. T. J. Chem. Educ. 87, 1348–1349 (2010).
Brown, D. G. & Boström, J. J. Med. Chem. 59, 4443–4458 (2016).
Quideau, S., Deffieux, D., Douat-Casassus, C. & Pouységu, L. Angew. Chem. Int. Ed. 50, 586–621 (2011).
Hassan, J., Sévignon, M., Gozzi, C., Schulz, E. & Lemaire, M. Chem. Rev. 102, 1359–1469 (2002).
Huang, Z. & Lumb, J.-P. ACS Catal. 9, 521–555 (2019).
Jurrat, M., Maggi, L., Lewis, W. & Ball, L. T. Nat. Chem. https://doi.org/10.1038/s41557-020-0425-4 (2020).
Gagnon, A., Dansereau, J. & Le Roch, A. Synthesis 49, 1707–1745 (2017).
Gagnon, A., Benoit, E. & Le Roch, A. in Science of Synthesis Knowledge Updates Vol. 4, 1–111 (Thieme, 2018).
Barton, D. H. R., Lester, D. J., Motherwell, W. B. & Barros Papoula, M. T. J. Chem. Soc. Chem. Commun. 246–247 (1980).
Suzuki, H., Murafuji, T. & Azuma, N. J. Chem. Soc. Perkin Trans. I 1593–1600 (1992).
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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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DOI: https://doi.org/10.1038/s41557-020-0434-3