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

Abstract

An efficient catalytic system using 1‐benzyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride and PdCl2 was developed for the cross‐coupling reaction of arylboronic acids with acyl chlorides. The catalytic amount of this homogeneous catalytic system affords the corresponding diaryl and alkyl aryl ketones in good to excellent yields under mild reaction conditions. Copyright © 2015 John Wiley & Sons, Ltd.

Recent Advances in Acyl Suzuki Cross-Coupling

“…In 2015, in continuation of their studies on 1-benzyl-4-aza-1-azonia-bicyclo[2.2.2]octane chloride-palladium chloride complex [(BeDABCO) 2 Pd 2 Cl 6 ], Rafiee and co-workers found that this catalyst was highly active for acylative cross-coupling of acyl chlorides with boronic acids (Scheme 2A) [20]. This reaction allowed for the use of various acyl chlorides and arylboronic acids under mild and phosphine-free conditions.…”

“…Recently, there have been major developments in the acyl Suzuki cross-coupling of aryl esters (Schemes [16][17][18][19][20]. There are several key advantages of using ester electrophiles in the acyl Suzuki cross-coupling, including (i) high-stability, (ii) prevalence in organic synthesis, (iii) opportunities for orthogonal cross-coupling strategies, (iv) reduction of toxic waste produced in the cross-coupling step.…”

Continuous flow synthesis of diaryl ketones by coupling of aryl Grignard reagents with acyl chlorides under mild conditions in the ecofriendly solvent 2-methyltetrahydrofuran

“…The conventional method is Friedel-Cras acylation of arenes, which has drawbacks such as the requirement for superstoichiometric amounts of Lewis acid and low regioselectivity. 9,10 Alternative synthetic approaches have been developed, including oxidation of secondary alcohols, 11,12 acylation of organometallic reagents, [13][14][15][16] transition-metal-catalyzed cross-coupling reactions of carboxylic acid derivatives with organometallic reagents, [17][18][19][20][21][22][23][24] palladium-catalyzed carbonylative cross-coupling reactions between aryl halides and related compounds with carbon nucleophiles, [25][26][27][28][29][30] acylation of (hetero)aryl halides with aldehydes, 31 decarboxylative cross-coupling reactions, 32,33 decarboxylative addition reactions, 33 and other uncommon reactions. 34 Unfortunately, there remain a number of limitations with regards to expensive catalysts, safety concerns, and environmentally practical considerations.…”

Synthesis, structure, and characterization of picolyl‐ and benzyl‐linked biphenyl palladium N‐heterocyclic carbene complexes and their catalytic activity in acylative cross‐coupling reactions

“…Cross‐coupling reaction of aryl boronic acids with carboxylic acid derivatives over palladium catalysts has emerged as a powerful tool for the synthesis of biaryl ketones . Reports by Yamamoto et al .…”