N-(o-Halophenyl)imidoyl chlorides and the corresponding imidates are easily prepared and can be utilized as complementary precursors for the synthesis of important heterocycles. The synthesis of N-substituted benzimidazoles was possible from the palladium-catalyzed reaction of both classes of substrate with a variety of N-nucleophiles. The use of the imidate precursor for the synthesis of N-substituted quinazolinones by incorporation of a palladium-catalyzed aminocarbonylation reaction has also been demonstrated. Both processes tolerate a wide range of functional groups.

No abstract

This article reviews the use of palladium-and coppercatalyzed 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.

Review: about 150 refs.

Palladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors. -Both pathways, which produce the desired N-heterocyclic skeletons, tolerate a broad spectrum of functionalities. -(SADIG, J. E. R.; FOSTER, R.; WAKENHUT, F.; WILLIS*, M. C.; J. Org. Chem. 77 (2012) 21, 9473-9486, http://dx.doi.org/10.1021/jo301805d ; Chem. Res. Lab., Univ. Oxford, Oxford OX1 3TA, UK; Eng.) -Jannicke 09-135