Palladium- and Copper-Catalyzed Aryl Halide Amination, Etherification and Thioetherification Reactions in the Synthesis of Aromatic Heterocycles

Abstract

This article reviews the use of palladium- and copper-catalyzed aryl halide amination, etherification and thioetherification processes in the synthesis of heteroaromatic molecules. The review is structured by the nature of the key C-X bond being formed, and then by heterocycle type. Where applicable individual heterocycles are further divided into syntheses based on intermolecular, intramolecular and cascade processes. In order to limit the length of the article, processes that do not deliver an aromatic heterocycle from the key C-X bond-forming event are excluded. Processes for the functionalization of intact heteroaromatics are also not included. 1 Introduction 2 Carbon-Nitrogen Bond Formation 2.1 Indoles 2.2 Carbazoles 2.3 Benzimidazoles and Benzimidazolones 2.4 Indazoles and Indazolones 2.5 Pyrroles 2.6 Pyrazoles 2.7 Oxazoles 2.8 Quinolones 2.9 Quinazolines, Quinazolinones and Quinazolinediones 2.10 Phenazines 2.11 Cinnolines 3 Carbon-Oxygen Bond Formation 3.1 Benzofurans 3.2 Benzoxazoles 3.3 Isocoumarins 4 Carbon-Sulfur Bond Formation 4.1 Benzothiophenes 4.2 Benzothiazoles 4.3 Oxathioles 5 Conclusion. © Georg Thieme Verlag Stuttgart · New York.