Synthesis of Ortho-alkoxy-aryl Carboxamides via Palladium-Catalyzed Aminocarbonylation |
| |
Authors: | Attila Takács Artur R. Abreu Andreia F. Peixoto Mariette Pereira |
| |
Affiliation: | 1. Department of Inorganic Chemistry , University of Pécs , Pécs, Hungary;2. Departamento de Quimica , Universidade de Coimbra , Coimbra, Portugal |
| |
Abstract: | Various aryl carboxamides with alkoxy substituents at the ortho-position, applicable as direct intermediates toward novel ligands, were synthesised via aminocarbonylation of aryl-iodides (2-iodoanisole, 5-chloro-7-iodo-8-methoxy-quinoline, and 5-chloro-7-iodo-8-benzyloxy-quinoline) in the presence of in situ generated palladium(0) catalysts. Simple primary and secondary amines as well as aminoacid esters were used as N-nucleophiles. The optimization of the reaction conditions allowed the preferential formation of carboxamides or ketocarboxamides by simple or double carbon monoxide insertion, respectively. A strong dependence of the chemoselectivity on carbon monoxide pressure was observed. |
| |
Keywords: | Aminocarbonylation carbon monoxide carbonylation iodo-aromatics palladium quinoline |
|
|