The effect of N-heterocyclic carbene ligands in the palladium-catalyzed cross-coupling reaction of K[C6F5BF3] with aryl iodides and aryl bromides

Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates

“…The main problem of these fluorinated phenylboronic acids is the rapid deboronation under basic conditions which can be circumvented by elaborate precatalysts such as second generation palladacycles developed by Buchwald and co-workers . As an alternative to polyfluorophenylboronic acids, lithium polyfluorophenyltrimethoxyborates and potassium polyfluorophenyltrifluoroborates − were proven to be effective coupling partners in cross coupling reactions and therefore were also able to introduce C 6 F 5 -groups into polyaryl compounds. Since highly fluorinated compounds are easier targets for hydrodefluorination compared to less fluorinated compounds, this has been exploited in C–F activation. , The high acidity of the corresponding hydrogens in these compounds can be used for C–H activation − and in combination with arenediazonium salts this was used for copper-catalyzed cross-coupling .…”

Suzuki–Miyaura Coupling Reactions of Fluorohalobenzenes

“…25,26 Traditional syntheses of fluorinated compounds are carried out mainly by two ways: either by C-F bond formation using fluorinating agents or by C-C bond formation using fluorinated substrates. A range of methods and reagents have been reported for transition-metal-catalyzed transformations of fluorinated substrates, e.g., arylation, 27 alkenylation, 28 olefination 29 and oxidative cross-coupling, 30,31 reactions with organochlorosilanes, 32,33 Grignard reagents, 34 potassium aryltrifluoroborates, [35][36][37] and organolithium reagents. 38 The Suzuki-Miyaura cross-coupling reaction of aryl/heteroarylboronic acids with simple aryl/heteroaryl halides is a commonly used method for preparing biaryl and heterobiaryl systems.…”

Pd‐catalyzed Desulfitative reaction of Aryltrifluoroborates with sodium Arenesulfinates in water

“…Traditionally, aryl halides are most widely used electrophilic reagents in Pd-catalyzed Suzuki cross-coupling reactions with organotrifluoroborates (Scheme 1, C-X cleavage). [16][17][18][19][20][21][22][23] Subsequently, the methods utilizing aryl tosylates which derived from the respective phenols in Suzuki coupling with organotrifluoroborates have been developed. The transformation proceeded via C-O bond cleavage instead of C-X bond (Scheme 1, C-O cleavage).…”