Copper-catalysed low-temperature water–gas shift reaction for selective deuteration of aryl halides,Chemical Science

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Copper-catalysed low-temperature water–gas shift reaction for selective deuteration of aryl halides
Chemical Science ( IF 7.6 ) Pub Date : 2021-09-17 , DOI: 10.1039/d1sc04259a
Wu Li ₁ , Ruiyang Qu ₁ , Weiping Liu ₁ , Florian Bourriquen ₁ , Stephan Bartling ₁ , Nils Rockstroh ₁ , Kathrin Junge ₁ , Matthias Beller ₁

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The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification of metabolites. Hence, methodologies for the synthesis of selectively labelled compounds continue to be a major area of interest for many scientists. Herein, we present a practical and stable heterogeneous copper catalyst, which permits for dehalogenative deuteration via water–gas shift reaction at comparably low temperature. This novel approach allows deuteration of diverse (hetero)aryl halides with good functional group tolerance, and no reduction of the aromatic rings or other easily reducible formyl and cyano groups. Multi-gram experiments show the potential of this method in organic synthesis and medicinal chemistry.

中文翻译：

铜催化低温水煤气变换反应用于芳基卤化物的选择性氘化

将氘原子引入有机化合物中对于基础化学、材料科学和制药行业的药物开发具有重要意义，特别是对于代谢物的鉴定和定量。因此，选择性标记化合物的合成方法仍然是许多科学家感兴趣的主要领域。在此，我们提出了一种实用且稳定的多相铜催化剂，它允许通过在相对较低的温度下进行水煤气变换反应。这种新方法允许氘代各种（杂）芳基卤化物具有良好的官能团耐受性，并且不会减少芳环或其他易于还原的甲酰基和氰基。多克实验显示了该方法在有机合成和药物化学中的潜力。

更新日期：2021-09-28

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