Synthesis of Deuterated 1,2,3-Triazoles

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• 作者：Hari K. Akula ; Mahesh K. Lakshman
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：October 19, 2012
• 年：2012
• 卷：77
• 期：20
• 页码：8896-8904
• 全文大小：455K
• 年卷期：v.77,no.20(October 19, 2012)
• ISSN：1520-6904

文摘

The copper-catalyzed azide鈥揳lkyne 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 CH₂Cl₂/D₂O, using the CuSO₄/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 H₂O and D₂O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H⁺ and D⁺ ion concentrations in H₂O and D₂O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.