A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

Wu, Ding-Chuan; Bai, Jing-Wen; Guo, Lei; Hu, Guang-Qi; Liu, Kaihui; Sheng, Fei-Fei; Zhang, Hong-Hai; Sun, Zhengyi; Shen, Kang; Liu, Xiang

doi:10.1016/j.tetlet.2020.152807

Cited by 13 publications

(5 citation statements)

References 66 publications

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“…While basic conditions or ruthenium catalysis had previously been used for the deuteration of terminal alkynes, in a recent report it was found that silver salts can also activate alkyne substrates for labeling processes at the terminal position (Scheme ). High deuterium incorporations are thus obtained under mild conditions and in the absence of other additives.…”

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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“…High reactivity for alkyne C(sp)-deuteration under neutral conditions would be favourable for the selective deuteration of alkyne-tagged probes for Raman imaging. 30,31…”

Section: Resultsmentioning

confidence: 99%

Iridium-catalyzed α-selective deuteration of alcohols

et al. 2022

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“…Since this work was carried out, a similar Ag + ‐catalysed procedure for the preparation of terminally deuterated alkynes has been published 18 . In that procedure, deuteration was achieved using deuterium oxide as donor and silver trifluoroacetate as catalyst in a dichloromethane/deuterium oxide mixture.…”

Section: Resultsmentioning

confidence: 99%

“…Since this work was carried out, a similar Ag +catalysed procedure for the preparation of terminally deuterated alkynes has been published. 18 In that procedure, deuteration was achieved using deuterium oxide as donor and silver trifluoroacetate as catalyst in a dichloromethane/deuterium oxide mixture. The procedure gives good recoveries and deuterium abundances for a range of propargyl ethers, propargylamines, and phenylacetylene analogues and could form an effective alternative to our procedure for those alkynes suited to the reaction conditions.…”

Section: F I G U R E 1 Labelling Of Terminal Alkynes By Catalytic Iso...mentioning

confidence: 99%

Practical approaches to labelling terminal alkynes with deuterium

Chan

Anwar

Lockley

2022

Labelled Comp Radiopharmac

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Base catalysed exchange with sodium hydroxide, calcium oxide or N,N,N,N‐tetramethylguanidine in deuterium oxide is a viable procedure for the preparation of terminally deuterated alkynes for those alkynes stable to strong base. The use of silver perchlorate as a catalyst is an alternative practical option when labelling alkynes which are sensitive to base or contain functionalities which would lead to labelling elsewhere in the molecule. Labelling with this catalyst takes place smoothly at ambient temperature in a mixture of N,N‐dimethylformamide and deuterium oxide.

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A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

Cited by 13 publications

References 66 publications

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Iridium-catalyzed α-selective deuteration of alcohols

Practical approaches to labelling terminal alkynes with deuterium

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