PALLADIUM-CATALYZED SUZUKI-MIYAURA CROSS-COUPLING REACTION OF AROMATIC ESTERS AND AROMATIC DIESTERS WITH ARYLBORONIC ACIDS

Abstract

The palladium-catalyzed cross-coupling reactions for the functionalization of the ester bond provides a significant overall improvement in the catalytic system as compared to aryl halides/pseudo-halides electrophilic coupling partners. Several pathways have been developed to construct C-C or C-X (-O,-N,-S,&-P) bonds that avoid pre-functionalization, hard reaction conditions, and waste production. These pathways include decarboxylation, decarbonylative, and non-decarbonylative coupling reactions. The non-decarbonylative coupling reaction of aromatic esters with organoboron compounds has emerged as a novel and valuable solution, providing new methodologies and synthetics in organometallic chemistry. More specifically, this type of reaction has shown promising results for synthesizing biaryl compounds and aryl diketones from aromatic esters. This study found that a series of novel aryl ketone and aryl diketone moieties can be formed via a non-decarbonylative Suzuki-Miyaura coupling reaction using readily available and inexpensive starting materials (e.g., phenyl benzoate, 1,4-diphenyl 1,4-benzenedicarboxylate, and 1,3-diphenyl 1,3-benzenedicarboxylate) with aryl boronic acids in the presence of [Pd(IPr)(𝞹-4- CF3C6H4-C3H5)Cl] precatalysts.