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A practical and environmentally friendly protocol for synthesis of α-deuterated carboxylic acids

Wennerberg, Johan LU and Dreisch, Klaus (2023) In Journal of Labelled Compounds and Radiopharmaceuticals 66(4-6). p.138-144
Abstract

α-deuterated carboxylic acids have been synthesized from the corresponding malonic acids via hydrogen/deuterium exchange and decarboxylation in presence of D2O. The method is general, mild and efficient and does not require organic solvents or other additives. Yields range between 83% and 94% and purification was not necessary. Starting materials were easy accessible and the α-deuterated carboxylic acids may easily be transformed to other labeled compounds such as alcohols, aldehydes, esters, and amides. Characterization with NMR confirmed purity and isotopic purity.

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author
and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
H labeling, decarboxylation, malonic acids, α-deuterated carboxylic acid
in
Journal of Labelled Compounds and Radiopharmaceuticals
volume
66
issue
4-6
pages
7 pages
publisher
John Wiley & Sons Inc.
external identifiers
  • pmid:36823686
  • scopus:85149390548
ISSN
0362-4803
DOI
10.1002/jlcr.4021
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2023 The Authors. Journal of Labelled Compounds and Radiopharmaceuticals published by John Wiley & Sons Ltd.
id
500b6714-2f7e-409b-8768-af21d08e77c1
date added to LUP
2024-01-12 14:10:03
date last changed
2025-05-11 20:26:57
@article{500b6714-2f7e-409b-8768-af21d08e77c1,
  abstract     = {{<p>α-deuterated carboxylic acids have been synthesized from the corresponding malonic acids via hydrogen/deuterium exchange and decarboxylation in presence of D<sub>2</sub>O. The method is general, mild and efficient and does not require organic solvents or other additives. Yields range between 83% and 94% and purification was not necessary. Starting materials were easy accessible and the α-deuterated carboxylic acids may easily be transformed to other labeled compounds such as alcohols, aldehydes, esters, and amides. Characterization with NMR confirmed purity and isotopic purity.</p>}},
  author       = {{Wennerberg, Johan and Dreisch, Klaus}},
  issn         = {{0362-4803}},
  keywords     = {{H labeling; decarboxylation; malonic acids; α-deuterated carboxylic acid}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{4-6}},
  pages        = {{138--144}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{Journal of Labelled Compounds and Radiopharmaceuticals}},
  title        = {{A practical and environmentally friendly protocol for synthesis of α-deuterated carboxylic acids}},
  url          = {{http://dx.doi.org/10.1002/jlcr.4021}},
  doi          = {{10.1002/jlcr.4021}},
  volume       = {{66}},
  year         = {{2023}},
}