Potassium acyltrifluoroborates (KATs) are increasingly important functional groups,a nd general methods for their preparation are of great current interest. We report abifunctional iminium reagent bearing both atin nucleophile and at rifluoroborate,w hichw as applied in chemoselective Pd 0 -catalyzed Migita-Kosugi-Stille cross-coupling reactions owitha ryl and vinyl halides.T his method gives access to previously inaccessible aromatic and a,b-unsaturated acyltrifluoroborates,i ncluding precursors to amino-acid derived KATs.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.Scheme 4. Analysis on the effect of copper. Scheme 5. Direct synthesis of a-aminotrifluoroborates from aryl iodides. Scheme 3. Synthesis of amino acid derived KATs by hydrogenation. Angewandte Chemie Communications
Kaliumacyltrifluoroborate (KATs) werden immer wichtigere funktionelle Gruppen, und somit werden aucha llgemeine Methoden füri hre Synthese bençtigt. Wirb erichten hier über ein bifunktionelles Iminiumreagenz, das sowohle in Zinn-Nukleophil als aucheine Trifluoroboratgruppe aufweist. Durchd iese Kombination kann man mit Aryl-und Vinylhalogeniden chemoselektive Pd 0 -katalysierte Migita-Kosugi-Stille-Kreuzkupplungen durchführen, um das entsprechende KATz ue rhalten. Diese Methode machte sz um ersten Mal mçglich, a,b-ungesättigte Acyltrifluoroborate sowieV orstufen zu Aminosäure-KATs herzustellen.
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