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

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journal contribution
posted on 17.12.2015, 03:46 by Michael Trose, Monica Dell’Acqua, Tommaso Pedrazzini, Valentina Pirovano, Emma Gallo, Elisabetta Rossi, Alessandro Caselli, Giorgio Abbiati
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.

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