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[Silver(I)(Pyridine-Containing Ligand)] Complexes As Unusual Catalysts for A3-Coupling Reactions

Author:
Trose, Michael, Dell’Acqua, Monica, Pedrazzini, Tommaso, Pirovano, Valentina, Gallo, Emma, Rossi, Elisabetta, Caselli, Alessandro, Abbiati, Giorgio
Source:
Journal of organic chemistry 2014 v.79 no.16 pp. 7311-7320
ISSN:
1520-6904
Subject:
aldehydes, alkynes, aniline, catalysts, chemical reactions, chemical structure, dielectric heating, ketones, ligands, organic chemistry, silver, synthesis
Abstract:
Two original macrocyclic silver(I)(pyridine-containing ligand) complexes [Ag(I)(Pc-L)] were synthesized and characterized. Their ability to catalyze the coupling among aldehydes, terminal alkynes and amines (A³-coupling) was demonstrated. The reaction could be performed under conventional as well as dielectric heating. The catalysts were effective in both cases, but dielectric heating allowed a lower catalyst loading and reduced ratio among reaction partners in shorter reaction times. The reaction scope was broad, including aryl/alkyl aldehydes, aryl/alkyl acetylenes and secondary aliphatic amines. Some unprecedented propargylamines have been prepared. The new catalytic system was also tested with more challenging coupling partners such as aniline and ketones.
Agid:
5502556