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. 2012 Oct 19;77(20):8896-904.
doi: 10.1021/jo301146j. Epub 2012 Sep 27.

Synthesis of deuterated 1,2,3-triazoles

Hari K Akula  1 , Mahesh K Lakshman
Affiliations

Synthesis of deuterated 1,2,3-triazoles

Hari K Akula et al. J Org Chem. .

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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Figures

Scheme 1
Scheme 1
Known syntheses of deuterated triazoles
Scheme 2
Scheme 2
Synthesis of poly- and fully-deuterated 1,2,3-triazoles
See this image and copyright information in PMC

References

    1. Huisgen R, Szeimies G, Möbius L. Chem. Ber. 1967;100:2492–2507.
    2. Huisgen R, Knorr R, Möbius L, Szeimies G. Chem. Ber. 1965;98:4041–4021.
    3. Huisgen R. Angew. Chem. Int. Ed. 1963;2:633–645.
    4. Huisgen R. Angew. Chem. Int. Ed. 1963;2:565–598.
    1. Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002;67:3057–3064. - PubMed
    1. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002;41:2596–2599. - PubMed

    1. For reviews see:

    2. Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001;40:2004–2021. - PubMed
    3. Gil MV, Arévalo MJ, López O. Synthesis. 2007:1589–1620.
    1. Ahlquist M, Fokin VV. Organometallics. 2007;26:4389–4391.

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