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Efficient labeling of organic molecules using 13C elemental carbon: universal access to 13C2-labeled synthetic building blocks, polymers and pharmaceuticals
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2019/12/19 , DOI: 10.1039/c9qo01357a
Maria S. Ledovskaya 1, 2, 3, 4 , Vladimir V. Voronin 1, 2, 3, 4 , Konstantin S. Rodygin 1, 2, 3, 4, 5 , Valentine P. Ananikov 1, 2, 3, 4, 5
Affiliation  

Among different types of labeling, 13C-labeled compounds are the most demanding in organic chemistry, life sciences and materials design. However, 13C-labeled organic molecules are very difficult to employ in practice due to extreme cost. The rather narrow range of labeled organic starting materials and the absence of universal synthetic building units further complicate the problem and make utilization of 13C-labeled molecules hardly possible in many cases. Here we report a versatile approach for 13C2-labeling of organic molecules starting with 13C elemental carbon: 13C carbon is applied for the synthesis of calcium carbide (Ca13C2), which is subsequently used to generate acetylene – a universal 13C2 unit for atom-economic organic transformations. Syntheses of labeled alkynes, O,S,N-functionalized vinyl derivatives, polymers and pharmaceutical substances were demonstrated. Elemental 13C carbon, as the chemically most simple source for 13C2-labeling, here was successfully combined with universal synthetic applicability of alkynes.

中文翻译:

使用13C元素碳对有机分子进行高效标记:普遍获得13C2标记的合成构件,聚合物和药物

在不同类型的标记中,13 C标记的化合物在有机化学,生命科学和材料设计中要求最高。然而,由于极高的成本,在实践中很难采用13 C标记的有机分子。标记的有机原料的范围很窄,而且没有通用的合成结构单元,这使问题进一步复杂化,在许多情况下几乎不可能利用13 C标记的分子。在这里,我们报告了一种从13 C元素碳开始的有机分子13 C 2标记的通用方法:13 C碳用于合成电石(Ca 13 C2),随后用于生成乙炔-一种用于原子经济有机转化的通用13 C 2单元。证明了标记的炔烃,O,S,N-官能化的乙烯基衍生物,聚合物和药物的合成。元素13 C碳作为化学上最简单的13 C 2标记来源,已成功地与炔烃的通用合成方法相结合。
更新日期:2020-02-18
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