ArticleThe Journal of organic chemistry2012
Synthesis of deuterated 1,2,3-triazoles.
Article in The Journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 31 citations in OpenAlex.
- Synthesis of Ethynyl Trifluoromethyl Sulfide and Its Application to the Synthesis of CFMolecules (Basel, Switzerland) · 2025Article
- Versatile Synthetic Platform for 1,2,3-Triazole Chemistry.ACS omega · 2022Review
- Triazole-Modified Peptidomimetics: An Opportunity for Drug Discovery and Development.Frontiers in chemistry · 2021Review
- Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles.Organic letters · 2013Article
Corrections and comments
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH(2)Cl(2)/D(2)O, using the CuSO(4)/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H(2)O and D(2)O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H(+) and D(+) ion concentrations in H(2)O and D(2)O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.
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Registered trials
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