Preparation of N‐alkylpyridinium aryl ketone derivatives via the surfactant promoted cross‐coupling reaction of N‐alkylpyridiniumboronic acids with carboxylic anhydride in water at room temperature

Abstract

The palladium (II) chloride catalyzed coupling reaction of N-alkylpyridiniumboronic acids with benzoic anhydride was carried out smoothly in water to give high yields of ketones without the use of a phosphine ligand. The reaction was conducted under mild conditions at room temperature. In this article, by focusing on the Suzuki reaction, it is shown how this method can impact modern synthetic chemistry, making reactions faster, easier and cleaner.

Yonemitsu-type condensations catalysed by proline and Eu(OTf)3

“…They act both as a solvent, by dissolving apolar compounds otherwise insoluble in water, and as a catalyst, by stabilising transition states through specic interactions and favouring the reactants encounter in a restricted environment. [11][12][13][14][15] Because cationic micelles increase the acidity of carbon acids by electrostatic as well as hydrophobic interactions with the enolate ion, 16,17 they are expected to favour the overall condensation. The reaction of indole, isobutyraldehyde, and methyl acetoacetate was chosen as a model reaction because it only works in 45% yield under classical conditions, 6 and is therefore worth optimising.…”

Synthesis and microwave‐assisted catalytic activity of novel bis‐benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross‐coupling reactions

“…The reactions have been realized by good yields, especially for aryl bromides 18–28. The ligand‐free systems consist of Pd(OAc) 2 , and base and solvents have also been used as a catalyst system in Suzuki coupling reactions 29–34. However, the Pd(OAc) 2 catalytic systems containing ligands have been shown to have more effective catalytic activity than ligand‐free Pd(OAc) 2 systems.…”

Transition‐Metal Catalyzed Coupling Reactions for the Synthesis of (Het)aryl Ketones: An Approach from their Synthesis to Biological Perspectives

“…The reaction was carried out in bromide which salts were used as surfactants in the absence of ligand using K 2 CO 3 as base for 12 h to give 99 % yield of desired product (Scheme 33). [54] Maerten and coworkers described the palladium (Pd) catalyzed synthesis of α ‐aryl pyridyl ketone by carbonylative cross‐coupling reaction between boronic acids and pyridine halides. This was three component reaction between pyridine halides, boronic acid and carbon monoxide in existence of Pd(OAc) 2 , anisole and Cs 2 CO 3 at 100 °C for 24 h to yield 83 % product.…”