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[20240129]

"Sulfonyl Azide Useful for Introduction of Azido and Diazo Groups"

2,4,6-Triisopropylbenzenesulfonyl azide (1) can be used as an electrophilic azidation agent or a diazotizing agent.1,2) When 1 reacts with a suitable base on a substrate containing a carbonyl group, an azido or diazo group can be introduced at the α-position. Recently, decarboxylative azidation reactions using visible light redox catalysts have also been reported.3) For example, using proline derivatives as substrates yield 2-azidopyrrolidine derivatives.

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References

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• 2) Symmetry in retrosynthetic analysis:(±)-pentalenolactone e methyl ester
  • D. C. Marcote, R. Street-Jeakings, E. Dauncey, J. J. Douglas, A. Ruffoni, D. Leonori, Org. Biomol. Chem. 2019, 17, 1839.
• 3) Photoinduced decarboxylative azidation of cyclic amino acids
  • J. P. F. Angeli, M. Schneider, B. Proneth, Y. Y. Tyurina, V. A. Tyurin, V. J. Hammond, N. Herbach, M. Aichler, A. Walch, E. Eggenhofer, D. Basavarajappa, O. Radmark, S. Kobayashi, T. Seibt, H. Beck, F. Neff, I. Esposito, R. Wank, H. Forster, O. Yefremova, M. Heinrichmeyer, G. W. Bornkamm, E. K. Geissler, S. B. Thomas, B. R. Stockwell, V. B. O’Donnell, V. E. Kagan, J. A. Schick, M. Conrad, Nat. Cell Biol. 2014, 16, 1180.