General and Greener Route to Ketones by Palladium-Catalyzed Direct Conversion of Carboxylic Acids with Organoboronic Acids

Abstract

Cross-coupling reaction of carboxylic acids with organoboron compounds catalyzed by palladium complexes in the presence of an activator such as dimethyl dicarbonate under mild conditions gives ketones in excellent yields except for certain substrates.

Carboxylic Acids as Substrates in Homogeneous Catalysis

“…[99] The more reactive dimethyl dicarbonate can also be used as activating reagent as an alternative to pivalic anhydride, in which case only the volatile coupling products CO 2 and methanol are formed (Scheme 43). As was shown in the work of Yamamoto et al [100] and ourselves [101] this reaction variant has advantages for more robust substrates, although is not compatible with quite so large a number of functional groups.…”

Synthesis of benzylpalladium complexes through C–O bond cleavage of benzylic carboxylates: Development of a novel palladium-catalyzed benzylation of olefins

“…As another application of the concept of the C-O bond cleavage to give acylpalladium complexes, we have developed a new process to prepare ketones and perfluoroketones by combination of the C-O bond cleavage in carboxylic anhydride with transmetallation with arylboronic acids as arylation reagents, providing with further examples of utility of the process involving the Pd-promoted C-O bond cleavage [9,10].…”

Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using EEDQ

“…To investigate the scope and limitations, the reaction of a variety of carboxylic acids with a variety of boronic acids in DMF 12 at 60 o C were studied and the results are listed in Table 2. Generally, the reactions work well with both electron rich and poor carboxylic acid as well as electron rich and poor boronic acid.…”