Highly selective catalytic Friedel–Crafts acylation and sulfonylation of activated aromatic compounds using indium metal

Highly efficient N‐Heterocyclic carbene–palladium complex‐catalyzed multicomponent carbonylative Suzuki reaction: novel practical synthesis of unsymmetric aryl ketones

“…1 Among many well-documented synthetic methods, such as Friedel-Crafts acylation of substituted aromatic rings, 2 the acylation of aryl metal species with functional carboxylic acid derivatives, 3 the transition metal-catalyzed three-component cross-coupling reaction between arylmetal reagents, carbon monoxide and aryl electrophiles is a straightforward and convenient route for the synthesis of unsymmetrical biaryl ketones. 4 Various arylmetal reagents including magnesium, 5 aluminum, 6 silicon, 7 tin 8 and boron derivatives 9 have been reported to undergo the carbonylative coupling.…”

Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

“…On the other hand, Pd-catalyzed crosscoupling reactions of acyl halides with organometallic reagents provides a direct procedure for the synthesis of isomeric ketones; a drawback is that Pd-catalysts are expensive and they are not recovered. [3][4][5][6][7][8] In 1993, Suzuki's group 9 reported a direct method (i.e., the carbonylative Suzuki coupling reaction) for the synthesis of aromatic ketones by the reaction of CO with an aryl halide and an arylboronic acid in the presence of PdCl 2 and Pd(dba) 2 (bis(dibenzylideneacetone)palladium). This reaction provides a versatile platform for the direct synthesis of aromatic ketones using boronic acids, which are generally non-toxic and stable to air and moisture.…”

Catalyst-free alkanoylation of aromatic rings via arylstannanes. Scope and limitations

“…It should be mentioned that, in the last years, different strategies have been developed which could be applied to the synthesis of these bulky ketones, for example, F-C reactions catalyzed by In [10], BiCl 3 [11] or silica [12]; cross-coupling reactions with organoboron reagents [13]; the reaction of acyl chlorides and Grignard reagents catalyzed by metal halides [14] and the Pd-mediated crosscoupling of a-oxocarboxylic acids and aryl bromides [15]. The method here proposed enables the high regioselective formation of bulky ketones without employing a catalyst, that is, a more ecofriendly acylation of aromatic rings.…”