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- Title
Metal‐Free Synthesis of Functional 1‐Substituted‐1,2,3‐Triazoles from Ethenesulfonyl Fluoride and Organic Azides.
- Authors
Giel, Marie‐Claire; Smedley, Christopher J.; Mackie, Emily R. R.; Guo, Taijie; Dong, Jiajia; Soares da Costa, Tatiana P.; Moses, John E.
- Abstract
The boom in growth of 1,4‐disubstituted triazole products, in particular, since the early 2000's, can be largely attributed to the birth of click chemistry and the discovery of the CuI‐catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1‐substituted‐1,2,3‐triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click‐inspired protocol for the synthesis of 1‐substituted‐1,2,3‐triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal‐free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1‐substituted‐1,2,3‐triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1‐substituted triazolium sulfonyl fluoride salts.
- Subjects
MICHAEL reaction; AZIDES; CLICK chemistry; FLUORIDES; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 3, p1197
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201912728