Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis

• Published in: Journal of the American Chemical Society Vol. 131; no. 9; pp. 3291 - 3306
• Main Authors: Campeau, Louis-Charles, Stuart, David R., Leclerc, Jean-Philippe, Bertrand-Laperle, Mégan, Villemure, Elisia, Sun, Ho-Yan, Lasserre, Sandrine, Guimond, Nicolas, Lecavallier, Melanie, Fagnou, Keith
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 11.03.2009; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Multidisciplinary; Cyclic N-Oxides - chemical synthesis; Cyclic N-Oxides - chemistry; Cyclic N-Oxides - pharmacology; Molecular Structure; Organometallic Compounds - chemistry; Palladium - chemistry; Physical Sciences; Protein Kinase Inhibitors - chemical synthesis; Protein Kinase Inhibitors - chemistry; Science & Technology; Sodium Channel Blockers - chemical synthesis; Sodium Channel Blockers - chemistry; Stereoisomerism; ASYMMETRIC CATALYSIS; BORONIC ACIDS; CROSS-COUPLING REACTIONS; ACTIVATION; HETEROCYCLES; ARYL HALIDES; EFFICIENT DEOXYGENATION; UNACTIVATED ARENES; LIGANDLESS CONDITIONS; C-H BONDS

Palladium-catalyzed direct arylation reactions are described with a broad range of azine and azole N-oxides. In addition to aspects of functional group compatibility, issues of regioselectivity have been explored when nonsymmetrical azine N-oxides are used. In these cases, both the choice of ligand...