Electrochemical α-deuteration of amides,Green Chemistry

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Electrochemical α-deuteration of amides
Green Chemistry ( IF 9.3 ) Pub Date : 2023-11-10 , DOI: 10.1039/d3gc02345a
Shulin Ning ₁ , Cheng Wu ₁ , Lianyou Zheng ₁ , Mian Liu ₁ , Yan Zhang ₁ , Xin Che ₁ , Jinbao Xiang _{1,

2}

Affiliation

Precise deuterium incorporation of bioactive molecules is highly desirable in order to improve ADME properties and monitor pharmacokinetics. Organic electrochemistry offers a powerful tool for molecular editing using electrons as traceless reagents. We herein present an electrochemical deuteration that can specifically modify the α-position of amides via an H/D exchange reaction under mild neutral conditions. This protocol provides an efficient tool for the rapid synthesis of α-deuterated amides in moderate to high yields with excellent levels of deuteration. In addition, the late-stage modification of drug molecules has been well demonstrated. Furthermore, the reduction of amides provides an efficient route to β-bisdeuterated amines, which are difficult to access by the existing methods. We envision that this on-demand deuterium incorporation will provide unique opportunities in biological research and therapeutics.

中文翻译：

酰胺的电化学 α-氘化

为了改善 ADME 特性并监测药代动力学，非常需要精确掺入生物活性分子的氘。有机电化学为使用电子作为无痕试剂的分子编辑提供了强大的工具。我们在此提出了一种电化学氘化方法，可以在温和中性条件下通过H/D 交换反应特异性修饰酰胺的 α 位。该方案为快速合成 α-氘代酰胺提供了一种有效的工具，具有中等到高产率和优异的氘化水平。此外，药物分子的后期修饰也得到了很好的证明。此外，酰胺的还原提供了生产β-双氘代胺的有效途径，而现有方法难以获得β-双氘代胺。我们预计，这种按需掺入氘将为生物研究和治疗提供独特的机会。

更新日期：2023-11-10

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