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.

[Silver(I)(Pyridine-Containing Ligand)] complexes as unusual catalysts for A3-coupling reactions / M. Trose, M. Dell'Acqua, T. Pedrazzini, V. Pirovano, E. Gallo, E. Rossi, A. Caselli, G. Abbiati. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 79:16(2014 Aug 15), pp. 7311-7320.

[Silver(I)(Pyridine-Containing Ligand)] complexes as unusual catalysts for A3-coupling reactions

M. Dell'Acqua
Secondo
;
T. Pedrazzini;V. Pirovano;E. Gallo;E. Rossi;A. Caselli
Penultimo
;
G. Abbiati
2014

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.
aldehyde-alkyne-amine; one-post synthesis; C-H activation; containing macrocyclic ligands; 3-component coupling reactions; quaternary carbon center; PC-L-asterisk; asymmetric cyclopropanation; efficient synthesis; terminal alkynes
Settore CHIM/06 - Chimica Organica
Settore CHIM/03 - Chimica Generale e Inorganica
15-ago-2014
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/237800
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