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

Abstract

The development of palladium(II)-catalyzed decarboxylative cross-coupling of α-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 α-oxo­carboxylic acids. Potassium aryl trifluoroborates were also transformed into ketones, amides, and esters with α-oxocarboxylic acids, oxamic acids, and oxalate monoesters, respectively, in modified catalytic systems. 1 Introduction 2 Palladium-Catalyzed Decarboxylative Cross-Coupling Through C–H Bond Functionalization 2.1 Direct ortho-Acylation of Acetanilides 2.2 Direct Acylation of 2-Phenylpyridines 2.3 Direct ortho-Acylation of Benzoic Acids 3 Transformation of Potassium Aryl Trifluoroborates into Ketones, Esters, and Amides 3.1 Formation of Aryl Ketones from Potassium Aryl Trifluoroborates 3.2 Preparation of Aryl Amides and Esters from Potassium Aryl Trifluoroborates 3.3 Mechanistic Studies 4 Conclusions and Outlook