Photo- and electro-catalytic deuteration of feedstock chemicals and pharmaceuticals: A review

Ou, Wei; Qiu, Chen; Su, Chenliang

doi:10.1016/s1872-2067(21)63928-1

Cited by 35 publications

(10 citation statements)

References 100 publications

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“…38 Consequently, it is a common strategy to introduce deuterium atoms into drug candidates, which might provide a good chance to tune their properties of absorption, distribution, metabolism, excretion, and toxicity (ADMET). Therefore, the development of efficient deuteration approaches under mild conditions has drawn huge attention in recent years, which has been well reviewed by Xie, 38 Beller, 39 Maiti, 40 Su, 41 Zhou, 42 and Tan, 43 respectively.…”

Section: Photocatalytic Decarboxylation Reaction To Synthesize Aldehydesmentioning

confidence: 99%

Recent advances in the photocatalytic synthesis of aldehydes

Wang

Liu

2023

Org. Chem. Front.

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Section: Photocatalytic Decarboxylation Reaction To Synthesize Aldehydesmentioning

confidence: 99%

Recent advances in the photocatalytic synthesis of aldehydes

Wang

Liu

2023

Org. Chem. Front.

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“…The presence of deuterium (D) can alert the pharmacokinetic pro les, reduce the dose, and lower the lethality of drugs due to the more stable C-D bond than the C-H bond. [1][2][3][4][5][6] In 2017, the US Food and Drug Administration approved the rst deuterated drug, deutetrabenazine (Austedo™), for an enhanced treatment of the Huntington's disease compared with its unlabeled version of tetrabenazine (Fig. 1a).…”

Section: Full Textmentioning

confidence: 99%

Field-induced concentration and low coordination-enhanced adsorption boost electroreductive deuteration of nitriles over copper nanotips

Cheng

et al. 2023

Preprint

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Electrochemical deuteration utilizing D2O is a promising room-temperature strategy for synthesizing deuterated molecules. At present, high Faradic efficiencies (FEs) at high reaction rates are extraordinarily significant but highly challenged. Here, high-curvature low-coordinated copper nanotips (LC-Cu NTs) are designed to enable electroreductive deuteration of α-deuterio aryl acetonitriles, in situ generated from fast α-H/D exchange of acetonitriles in D2O, to α,β-deuterio arylethyl primary amines with 90% FE and 0.11 mmol h-1 cm-2, greatly outperforming the reported data and other Cu counterparts. The increased electric fields of the nanotips concentrate nitriles and K+(D2O)n, and low-coordination sites promote nitriles and D2O adsorption, thus facilitating nitrile deuteration with an excellent reaction rate. The higher coupling energy barrier of active hydrogen atoms at low-coordination sites restricts the D2 evolution, accounting for the outstanding FE. The wide substrate scope, easy gram-scale synthesis, and facile preparation of d4-melatonin with enhanced antitumor and antioxidation effects highlight its great promise. Furthermore, the application of LC-Cu NTs in other deuteration reactions with improved reaction rates and FEs rationalizes the design concept.

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“…The integration of deuterium atoms into organic molecules is a crucial area of research for the synthetic and medicinal industries. [ 1‐5 ] Generally, substituting hydrogen with deuterium can enhance pharmacokinetics, augment active metabolites, impede the conversion between chiral drug isomers, and obstruct drug‐drug interactions. Deuterium atoms also serve as prevalent tracers for elucidating drug metabolism pathways.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Design, Synthesis and Application of a Robust d₃‐Methylthiolating Reagent^†

et al. 2023

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Comprehensive SummaryA deuterated methylthiolating reagent with a broad spectrum, designated as DMTP, has been ingeniously formulated. This new reagent can be produced with high efficiency through the simple combination of commercially available methyl 3‐thiopropanoate and CD3I. This novel SCD3 reagent exhibits excellent reactivity with electrophiles such as alkyl iodides, benzyl chlorides, aryl halides (I, Br) and aryl triflates, resulting in high levels of deuterium content (99% D). Representative deuterated methylthiolated biomolecules, such as Sulfoxaflor, have been synthesized for use in pharmaceutical discovery and development.This article is protected by copyright. All rights reserved.

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Photo- and electro-catalytic deuteration of feedstock chemicals and pharmaceuticals: A review

Cited by 35 publications

References 100 publications

Recent advances in the photocatalytic synthesis of aldehydes

Recent advances in the photocatalytic synthesis of aldehydes

Field-induced concentration and low coordination-enhanced adsorption boost electroreductive deuteration of nitriles over copper nanotips

Design, Synthesis and Application of a Robust d₃‐Methylthiolating Reagent^†

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Photo- and electro-catalytic deuteration of feedstock chemicals and pharmaceuticals: A review

Cited by 35 publications

References 100 publications

Recent advances in the photocatalytic synthesis of aldehydes

Recent advances in the photocatalytic synthesis of aldehydes

­Field-induced concentration and low coordination-enhanced adsorption boost electroreductive deuteration of nitriles over copper nanotips

Design, Synthesis and Application of a Robust d3‐Methylthiolating Reagent†

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Product

Resources

About

Field-induced concentration and low coordination-enhanced adsorption boost electroreductive deuteration of nitriles over copper nanotips

Design, Synthesis and Application of a Robust d₃‐Methylthiolating Reagent^†