Tritiodefluorination of alkyl C─F groups

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00510965" target="_blank" >RIV/61388963:_____/19:00510965 - isvavai.cz</a>
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/abs/10.1002/jlcr.3782" target="_blank" >https://onlinelibrary.wiley.com/doi/abs/10.1002/jlcr.3782</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/jlcr.3782" target="_blank" >10.1002/jlcr.3782</a>

Result language
angličtina
Original language name
Tritiodefluorination of alkyl C─F groups
Original language description
A straightforward methodology of fluorine substitution by tritium/deuterium is reported. The described method is selective towards the F─C (sp3) group and leaves both the aromatic F─C (sp2) and F2─C (sp3) moieties unaffected. Alkylfluorides, readily synthesized from appropriate alcohols by treatment with diethylaminosulfur trifluoride (DAST) reagent in an overall yield up to 76%, undergoes activation with the boron‐based Lewis acid B(C6F5)3, and stoichiometric in situ reduction with a tritide/deuteride reagent—the [TMP2(3)H][2(3)HB(C6F5)3] system of frustrated Lewis pair. This methodology provides an isolated yield of up to 93% of regio‐specifically labeled small organic compounds with superior 2H‐enrichment of over 95%. The specific activity of prepared 1‐(2‐[3H]‐ethyl)naphthalene was determined at 29.0 Ci/mmol. The site selectivity of the Lewis acid/ [TMP2(3)H][2(3)HB(C6F5)3] approach is orthogonal to currently used methods and allows for isotopic labeling of complementary positions in molecules. Reported labeling methodology proceeds well at ultra‐mild reaction conditions (220 mbar of T2), allowing very low consumption of the radioactive source (4.2 Ci/156 GBq), and producing limited amount of radioactive waste.
Czech name
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Czech description
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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

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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