A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki–Miyaura type of coupling reaction

A versatile method for the synthesis of diaryl and alkyl aryl ketones via palladium‐catalysed cross‐coupling reaction of arylboronic acids with acyl chlorides

“…Recently, palladium‐catalysed cross‐coupling of boronic acids with carboxylic derivatives has been developed as a powerful protocol for the regioselective synthesis of aromatic ketones . This approach is superior to the previous methods in terms of reaction conditions, selectivity, efficiency and functional group compatibility and also non‐toxicity, thermal, air and moisture stability and commercial availability of organoboron compounds as starting materials.…”

“…Bumagin and co‐workers described the synthesis of aromatic ketones via ligandless and phosphine‐free palladium‐catalysed coupling of acyl chlorides with arylboronic acids in aqueous acetone . There are several alternative procedures for this cross‐coupling reaction under various conditions, such as in aqueous media, anhydrous reaction and solvent‐free conditions …”

“…[15,16] Recently, palladium-catalysed cross-coupling of boronic acids with carboxylic derivatives has been developed as a powerful protocol for the regioselective synthesis of aromatic ketones. [17][18][19][20][21][22][23][24][25][26] This approach is superior to the previous methods in terms of reaction conditions, selectivity, efficiency and functional group compatibility and also non-toxicity, thermal, air and moisture stability and commercial availability of organoboron compounds as starting materials. Liebeskind and Srogl in 2000 developed a mild and general method for the palladium-catalysed, copper-mediated coupling of thiol esters and boronic acids under base-free conditions.…”

“…[32] There are several alternative procedures for this cross-coupling reaction under various conditions, such as in aqueous media, [33,34] anhydrous reaction [35][36][37] and solvent-free conditions. [38] Generally, the combination of palladium catalysts with phosphine and carbene ligands results in high efficiency in coupling reactions. However, most phosphine ligands are air-sensitive, expensive and require an inert environment and high catalyst loading of palladium source in carrying out the reaction.…”

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

“…[16,17] Water is compatible with most of the known palladium-catalyzed reactions, [18] but the low solubility of the majority of organic compounds in water is a major problem. [19] Yamamoto et al [20] , Ghosh et al [21] and Patil et al [22] independently reported a new method for obtaining aryl ketones under mild conditions, based on the cleavage of the C-O bond of carboxylic anhydrides or acyl chlorides in the presence of palladium catalysts. Nevertheless less active carboxylic derivatives, or carboxylic acids, require activation by phosphine ligands.…”