Palladium-Catalyzed Selective meta-C-H Deuteration of Arenes: Reaction Design and Applications

被引：50

作者：

Bag, Sukdev ^{[1
]}

Petzold, Martin ^{[2
]}

Sur, Aishanee ^{[1
]}

Bhowmick, Suman ^{[1
]}

Werz, Daniel B. ^{[2
]}

Maiti, Debabrata ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 40期

关键词：

deuterium; C-H activation; pharmaceuticals; pyrimidine-based directing group; template synthesis; BOND FUNCTIONALIZATIONS; H/D EXCHANGE; DEUTERIUM; DRUG; OLEFINATION; METABOLISM; ACTIVATION; TRITIATION; COMPLEXES; DISCOVERY;

D O I：

10.1002/chem.201901317

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：9433 / 9437

页数：5

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