Palladium-Catalyzed Selective meta-C-H Deuteration of Arenes: Reaction Design and Applications
Palladium-Catalyzed Selective meta-C-H Deuteration of Arenes: Reaction Design and Applications
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DOI：
10.1002/chem.201901317
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发表时间：
2019-07-17
影响因子：
4.3
通讯作者：
Maiti, Debabrata
中科院分区：
文献类型：
--
作者：
Bag, Sukdev;Petzold, Martin;Maiti, Debabrata
氘标记的化合物在动力学研究和制药工业中有着广泛的应用。一种易于去除的嘧啶基助剂已被用于芳烃的间位-C-H氘代反应。使用市售的[D-1]-和[D-4]-乙酸的Pd-催化的氘化的范围已经通过其在苯乙酸和苯甲磺酸酯衍生物中的应用得到证明。详细的机制研究使我们探索非速率决定C-H活化步骤的可逆性。本研究的间氘掺入说明模板形态的选择性。这种方法的适用性已被证明是由选择性氘掺入到各种药物。
Deuterium-labeled compounds find wide applications in kinetic studies, and within the pharmaceutical industry. An easily removable pyrimidine-based auxiliary has been employed for the meta-C-H deuteration of arenes. The scope of this Pd-catalyzed deuteration using commercially available [D-1]- and [D-4]-acetic acid has been demonstrated by its application in phenylacetic acid and phenylmethanesulfonate derivatives. A detailed mechanistic study led us to explore the reversibility of the non-rate determining C-H activation step. The present study of meta-deuterium incorporation illustrates the template morphology in terms of selectivity. The applicability of this method has been demonstrated by the selective deuterium incorporation into various pharmaceuticals.