Tritiodefluorination of alkyl C─F groups

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Tritiodefluorination of alkyl C─F groups

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Tritiodefluorination of alkyl C─F groups

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Labelled Compounds and Radiopharmaceuticals

ISSN

0362-4803

e-ISSN

—

Svazek periodika

62

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

743-750

Kód UT WoS článku

000492827500008

EID výsledku v databázi Scopus

2-s2.0-85069682298