Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, New York 10031-9198, USA.
J Org Chem. 2012 Oct 19;77(20):8896-904. doi: 10.1021/jo301146j. Epub 2012 Sep 27.
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.
铜催化的叠氮-炔环加成（CuAAC）是一种将氘原子选择性地引入 1,2,3-三唑结构的 C-5 位置的高效方法。炔烃和叠氮化物的反应可以在 CH(2)Cl(2)/D(2)O 的两相介质中方便地进行，使用 CuSO(4)/Na 抗坏血酸盐体系。该方法的温和性使其适用于相对复杂的底物，如核苷。观察到良好的产率和高氘原子掺入水平。在等摩尔 H(2)O 和 D(2)O 中进行的反应显示出与氘相比，氢原子的掺入量增加了 2.7 倍。这与 H(2)O 和 D(2)O 中的 H(+)和 D(+)离子浓度分别一致。使用适当氘化的前体，可以组装部分至完全氘化的三唑，其中最终的氘原子在形成三唑的步骤中掺入。
