Frustrated Lewis pairs: A real alternative to deuteride/tritide reductions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00510964" target="_blank" >RIV/61388963:_____/19:00510964 - isvavai.cz</a>
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/abs/10.1002/jlcr.3774" target="_blank" >https://onlinelibrary.wiley.com/doi/abs/10.1002/jlcr.3774</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/jlcr.3774" target="_blank" >10.1002/jlcr.3774</a>
Alternative languages
Result language
angličtina
Original language name
Frustrated Lewis pairs: A real alternative to deuteride/tritide reductions
Original language description
Deuterium- and tritium-labeled compounds play a principal role in tracing of biologically active molecules in complicated biochemical systems. The state-of-the-art techniques using noble metal catalysts or strong reducing agents often suffers from low functional group tolerances, poor selectivity, tricky or multistep synthesis of reagents, and low specific activity of the labeled product. Herein, we demonstrate a mild and nonmetallic technique of deuteration and tritiation of polarized double bonds, such as carbonyl compounds, yielding labeled alcohols of high specific activities. This one-pot synthesis uses carrier-free hydrogen gas in situ activated by a freshly prepared frustrated Lewis pair, generating reducing reagents. This labeling strategy shows better selectivity and functional group tolerances compared with current reductive methods. Reported is an example of the selective reduction of the aldehyde moiety of 3-acetylbenzaldehyde. What makes this technology groundbreaking is its mildness, selectivity, and generation of limited amount of radioactive waste as almost no byproducts were generated after use of (B(C6F5)(3)H-3)((HTMP)-H-3) reducing reagent. Radiochemical purity of desired H-3-labeled product in a crude reaction mixture was determined of over 94%. This work provides, to the community of radiochemists, a practical protocol for frustrated Lewis pairs (FLP)-assisted deuterium/tritium labeling technology.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10406 - Analytical chemistry
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Labelled Compounds and Radiopharmaceuticals
ISSN
0362-4803
e-ISSN
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Volume of the periodical
62
Issue of the periodical within the volume
11
Country of publishing house
GB - UNITED KINGDOM
Number of pages
14
Pages from-to
729-742
UT code for WoS article
000492827500007
EID of the result in the Scopus database
2-s2.0-85068448329