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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

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10406 - Analytical chemistry

Result continuities

  • Project

  • 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

  • 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