Palladium-catalyzed directed synthesis of <i>ortho</i>-deuterated phenylacetic acid and analogues

Manna, Priyadarshi; Kundu, Mrinalkanti; Roy, Ashis; Adhikari, Susanta

doi:10.1039/d1ob00663k

Cited by 3 publications

(1 citation statement)

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“…The economy of the deuterium source was further improved in a recently published ruthenium biscarboxylate-catalyzed ortho -directed benzoic acid deuteration, which only requires 10 equiv of deuterium oxide, while achieving high levels of deuteration (Scheme c) . Harnessing this deuterium source under palladium-catalyzed conditions is more challenging as seen in a recent report in which a more strongly coordinating bidentate pyridone directing group is needed to access ortho -deuterated phenylacetic amides …”

Section: Hydrogen Isotope Exchangementioning

confidence: 99%

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

et al. 2022

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Organic compounds labeled with hydrogen isotopes play a crucial role in numerous areas, from materials science to medicinal chemistry. Indeed, while the replacement of hydrogen by deuterium gives rise to improved absorption, distribution, metabolism, and excretion (ADME) properties in drugs and enables the preparation of internal standards for analytical mass spectrometry, the use of tritium-labeled compounds is a key technique all along drug discovery and development in the pharmaceutical industry. For these reasons, the interest in new methodologies for the isotopic enrichment of organic molecules and the extent of their applications are equally rising. In this regard, this Review intends to comprehensively discuss the new developments in this area over the last years (2017−2021). Notably, besides the fundamental hydrogen isotope exchange (HIE) reactions and the use of isotopically labeled analogues of common organic reagents, a plethora of reductive and dehalogenative deuteration techniques and other transformations with isotope incorporation are emerging and are now part of the labeling toolkit.

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Section: Hydrogen Isotope Exchangementioning

confidence: 99%

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

et al. 2022

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Recent advances in late‐stage selective deuteration for drug development

Wang,

Luo,

Luo

et al. 2024

Applied Organom Chemis

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Deuteration has emerged as a significant method for investigating kinetic isotope effects in chemical reactions. In recent years, research on deuteration has revealed that this reaction often alters the pharmacokinetic or toxicological properties of drug molecules, thereby enhancing their therapeutic effect. Therefore, deuteration is considered as a potential avenue for drug research direction. Since the approval of the first deuterated drug, “deutetrabenazine,” by the American Food and Drug Administration (FDA) in 2017, deuteration has been applied in the development of a variety of novel drugs. Research on deuteration technology has matured with the publication of numerous deuteration strategies. This article reviews recently reported strategies for late‐stage selective deuteration, discusses the challenges associated with current deuteration strategies, and presents future prospects for the synthesis of deuterated drugs.

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