Bag Sukdev, Petzold Martin, Sur Aishanee, Bhowmick Suman, Werz Daniel B, Maiti Debabrata
Department of Chemistry, Indian Institute of Technology Bombay, Powai, 400076, Mumbai, India.
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
Chemistry. 2019 Jul 17;25(40):9433-9437. doi: 10.1002/chem.201901317. Epub 2019 May 9.
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 ]- and [D ]-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.
氘标记化合物在动力学研究以及制药行业中有着广泛的应用。一种易于去除的嘧啶基辅助剂已被用于芳烃的间位C-H氘代反应。使用市售的[D] -和[D] -乙酸进行的这种钯催化氘代反应的范围，已通过其在苯乙酸和苯甲磺酸酯衍生物中的应用得到了证明。一项详细的机理研究促使我们探索非速率决定步骤的C-H活化的可逆性。目前关于间位氘掺入的研究从选择性方面说明了模板形态。该方法的适用性已通过将氘选择性掺入各种药物中得到了证明。
