Li Wu, Qu Ruiyang, Liu Weiping, Bourriquen Florian, Bartling Stephan, Rockstroh Nils, Junge Kathrin, Beller Matthias
Leibniz-Institut für Katalyse e.V. Albert-Einstein-Straße 29a 18059 Rostock Germany
Chem Sci. 2021 Sep 17;12(42):14033-14038. doi: 10.1039/d1sc04259a. eCollection 2021 Nov 3.
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 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.
将氘原子引入有机化合物对于基础化学、材料科学以及制药行业药物开发（特别是用于代谢物的鉴定和定量）具有重要意义。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，我们展示了一种实用且稳定的多相铜催化剂，它能够在相对较低的温度下实现脱卤氘化水煤气变换反应。这种新方法允许对各种（杂）芳基卤化物进行氘化，具有良好的官能团耐受性，并且不会使芳环或其他易于还原的甲酰基和氰基还原。多克规模的实验表明了该方法在有机合成和药物化学中的潜力。
