Menu
Abstract: Carboxylic acids are versatile organic compounds in nature, and it shares a number of features with boronic acids, which makes boronic acids potent bioisosteres in medicinal chemistry.1a,b Organoboron compounds are widely recognized not only for their use in cross-coupling reactions but also for their essential applications in materials science and for the synthesis of boronic acid drugs.2a,b Traditionally, C-B bonds are constructed by hydroboration of alkenes,3 Miyaura borylation,4 transmetalation5 and conjugate addition.6 Therefore, the conversion of carboxylic acid groups to boronic acids could afford an important class of molecules. The transformation of carboxylic acids to corresponding N-hydroxypthalimide ester followed by the decarboxylative couplingwith boronates results in the formation of the corresponding boronic acid derivatives.7a-c The details of these works will be discussed.

References:

  1. (a) Patra, T.; Maiti, D. Eur. J.2017, 23, 7382. (b) Ballatore, C.; Huryn, D. M.; Smith 3rd, A. B. ChemMedChem2013, 8, 385.
  2. (a) Brooks, W. L. A.; Sumerlin, B. S. Rev. 2016, 116, 1375. (b)Trippier, P. C.; McGuigan, C. Med.Chem.Comm.2010,1, 183.
  3. Vogels, C. M.; Westcott, S. A. Org. Chem. 2005, 9, 687.
  4. Atack, T. C.; R. Lecker, M. S.; Cook, P. Am. Chem. Soc. 2014,136, 9521.
  5. Brown, H. C.; Cole, T. E. Organometallics1983, 2,
  6. Lee, K. S.; Zhugralin, A. R.;Hoveyda, A. H. Am. Chem. Soc. 2009,131, 7253.
  7. (a)Fawcett, A.; Pradeilles, J.; Wang, Y.; Mutsuga, T.; Myers, E. L.; Aggarwal, V. K. Science2017,357, 283. (b) Li, C.; Wang, J.; Barton, L.M.; Yu, S.; Tian, M.; Peters, D.S.; Kumar, M.; Antony, W.Y.; Johnson, K.A.; Chatterjee, A.K.; Yan, M.; Baran, P.S. Science 2017,356, (c) Candish, L.; Teders, M.; Glorius, F.J. Am. Chem. Soc. 2017, 139, 7440.