Simple, Stable, and Easily Accessible Well‐Defined CuCF₃ Aromatic Trifluoromethylating Agents

Abstract

Gib mir ein F: [(Ph3P)3Cu(CF3)] (siehe Schema), ein seltenes gut definiertes Kupfer(I)‐Trifluormethylierungsagens, ist außerordentlich einfach in über 90 % Ausbeute zugänglich, im festen Zustand luftstabil und lange lagerbar. Außerdem eignet es sich als Ausgangsmaterial für die Synthese anderer CuCF3‐Komplexe wie [(phen)Cu(PPh3)(CF3)].

Introduction of Fluorine and Fluorine‐Containing Functional Groups

“…The first report of the copper‐mediated trifluoromethylation of aryl iodides with TMSCF 3 /KF363 by Urata and Fuchikami laid the foundation for trifluoromethylation/cross‐coupling with trifluoromethyltrialkylsilanes. Aryl halides in conjunction with trifluoromethylorganosilanes can react with the copper carbene complexes 4.1 and 4.2 described by Vicic and co‐workers (Scheme ),364 copper/silver co‐catalysts by Weng et al.,361 copper–nitrogenous ligand catalysts by Amii and co‐workers,365 isolated stoichiometric copper–phenanthroline complexes by Hartwig and co‐workers (Scheme ),366 and stoichiometric copper–phosphine complexes by Grushin and co‐workers (Scheme )367 to afford trifluoromethylated arenes. The method of Hartwig and co‐workers is the most functional‐group tolerant and allows the trifluoromethylation of electron‐poor, electron‐rich, and even ortho , ortho ‐disubstituted arenes, while the catalytic system of Amii and co‐workers utilizes only 10 mol % of the copper catalyst to afford trifluoromethylated arenes in 44–99 % yield.…”

Tamed Arene and Heteroarene Trifluoromethylation

“… Trifluoromethylation of arenes with well‐defined sources of CuCF 3 , described by the groups of Vicic,10a Grushin,10b and Hartwig,10c, d (top) and of Grushin11 (bottom). Bpin=pinacolylboryl.…”

Die Trifluormethylierung von Arenen und Heteroarenen

“… Trifluormethylierung von Arenen mit wohldefinierten CuCF 3 ‐Quellen, wie sie die Gruppen von Vicic,10a Grushin10b und Hartwig,10c, d (oben) sowie Grushin11 (unten) beschrieben haben. Bpin=Pinacolylboryl.…”