Direct Sulfenylation of the Purine C8-H Bond with Thiophenols.,The Journal of Organic Chemistry

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Direct Sulfenylation of the Purine C8-H Bond with Thiophenols.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-14 , DOI: 10.1021/acs.joc.9b03115
Wei Jiang ₁ , Juanping Zhuge ₁ , Jianxiao Li ₁ , Gary Histand ₂ , Dongen Lin ₁

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The one-step copper-mediated regioselective formation of the C8-S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na2CO3 and stoichiometric CuCl and 1,10-phenanthroline monohydrate. This method provides an economical, easy-to-handle, and effective method for the synthesis of 8-sulfenylpurine derivatives in moderate to excellent yields. The reaction is selective for C8 over C2 and C6. It also tolerates a free amine on the purine, and it has a wide substrate scope.

中文翻译：

嘌呤C8-H键与硫酚的直接亚磺酰基化。

在1.0当量的Na2CO3和化学计量的CuCl和1,10-菲咯啉一水合物的存在下，使用空气作为绿色氧化剂，可实现嘌呤衍生物与芳硫醇的C8-S键的一步铜介导的区域选择性形成。该方法提供了经济，易于操作且有效的方法，以中等至极好的收率合成了8-亚磺酰基嘌呤衍生物。该反应对C8的选择性高于对C2和C6的选择性。它还可以耐受嘌呤上的游离胺，并且具有广泛的底物范围。

更新日期：2020-01-14

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