Palladium-Catalyzed Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids and Their Derivatives

The development of palladium(II)-catalyzed decarboxylative cross-coupling of alpha-oxocarboxylic acids and their derivatives is summarized in this account. Acetanilides, 2-phenyl-pyridines, and benzoic acids were found to be suitable substrates for direct acylation through decarboxylative cross-coupling with alpha-oxo-carboxylic acids. Potassium aryl trifluoroborates were also transformed into ketones, amides, and esters with alpha-oxocarboxylic acids, oxamic acids, and oxalate monoesters, respectively, in modified catalytic systems. 1Introduction 2Palladium-Catalyzed Decarboxylative Cross-Coupling Through C-H Bond Functionalization 2.1Direct ortho-Acylation of Acetanilides 2.2Direct Acylation of 2-Phenylpyridines 2.3Direct ortho-Acylation of Benzoic Acids 3Transformation of Potassium Aryl Trifluoroborates into Ketones, Esters, and Amides 3.1Formation of Aryl Ketones from Potassium Aryl Trifluoroborates 3.2Preparation of Aryl Amides and Esters from Potassium Aryl Trifluoroborates 3.3Mechanistic Studies 4Conclusions and Outlook