Parallel Minisci Reaction of gem-Difluorocycloalkyl Building Blocks

Parallel Minisci reactions of nonfluorinated and gem-difluorinated C4–C7 cycloalkyl building blocks (trifluoroborates and carboxylic acids) with a series of electron-deficient heterocycles were studied. A comparison of the reaction’s outcome revealed better product yields in the case of carboxylic a...

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Published inACS Organic & Inorganic Au Vol. 4; no. 4; pp. 424 - 431
Main Authors Holovach, Serhii, Poroshyn, Illia, Melnykov, Kostiantyn P., Liashuk, Oleksandr S., Pariiska, Olena O., Kolotilov, Sergey V., Rozhenko, Alexander B., Volochnyuk, Dmytro M., Grygorenko, Oleksandr O.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 07.08.2024
Subjects
radical reactions
trifluoroborates
carboxylic acids
cycloalkanes
fluorine
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Summary:Parallel Minisci reactions of nonfluorinated and gem-difluorinated C4–C7 cycloalkyl building blocks (trifluoroborates and carboxylic acids) with a series of electron-deficient heterocycles were studied. A comparison of the reaction’s outcome revealed better product yields in the case of carboxylic acids as the radical precursors in most cases, albeit these reagents were used with three-fold excess under optimized conditions. The nature of the heterocyclic core was found to be important for successful incorporation of the cycloalkyl fragment. The impact of the CF2 moiety on the oxidation potential of fluorinated cycloalkyl trifluoroborates and the reaction outcome, in general, was also evaluated.
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ISSN:2694-247X
2694-247X
DOI:10.1021/acsorginorgau.4c00028