4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 16, Pages 7311-7320

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo500981r

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Two original macrocyclic silver(1)(pyridine-containing ligand) complexes [Ag(I)(Pc-L)] were synthesized and characterized. Their ability to catalyze the coupling among aldehydes, terminal alkynes and amines (A(3)-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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