Synfacts 2019; 15(12): 1435
DOI: 10.1055/s-0039-1691124
Chemistry in Medicine and Biology
© Georg Thieme Verlag Stuttgart · New York

Click Chemistry for the Synthesis of Azides

Contributor(s):
Dirk Trauner
,
Belinda E. Hetzler
Meng G, Guo T, Ma T, Zhang J, Shen Y, Sharpless KB. * Dong J. * Shanghai Institute of Organic Chemistry, P. R. of China
Modular Click Chemistry Libraries for Functional Screens using a Diazotizing Reagent.

Nature 2019;
574: 86-89
Further Information

Publication History

Publication Date:
18 November 2019 (online)

 

Significance

Copper-catalyzed azide alkyne click chemistry (CuAAC) is a powerful bioorthogonal reaction that provides triazole products in very high yields. A significant limitation is the restricted access to the azide precursors because azide preparation with NaN3 or TfN3 suffers from long reaction times, toxicity, or risk of explosion. The authors present a new, highly reactive diazo transfer reagent that enables rapid and safe access to azides from amines.


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Comment

Previously reported fluorosulfuryl imidazolium triflate salt (Guo et al. Angew. Chem. Int. Ed. 2018, 57, 2605) was treated with NaN3 to generate fluorosulfuryl azide 1 in situ. In an optimized solvent system (DMF–MTBE–H2O), 1 undergoes diazo transfer to a broad variety of amines in a click chemistry fashion.


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