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Three‐Component Coupling of Aldehydes, Amines, and Alkynes Catalyzed by Oxidized Copper Nanoparticles on Titania
Author(s) -
Albaladejo María José,
Alonso Francisco,
Moglie Yanina,
Yus Miguel
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200090
Subject(s) - chemistry , copper , alkyne , catalysis , amine gas treating , ketone , nanoparticle , solvent , coupling reaction , combinatorial chemistry , organic chemistry , polymer chemistry , nanotechnology , materials science
Copper nanoparticles (mainly as Cu 2 O) on titania have been shown to catalyze the multicomponent synthesis of propargylamines from aldehydes, amines, and alkynes (A 3 coupling) effectively at 70 °C under solvent‐free conditions. Both aromatic and aliphatic aldehydes and alkynes have been combined with secondary amines to provide a wide range of propargylamines in moderate to excellent yields. Two examples of ketone/amine/alkyne (KA 2 ) coupling are also included. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol‐%), and exhibits higher catalytic activity than some commercially available copper sources. Some mechanistic aspects of the reaction have also been examined, which have unveiled the participation of copper(I) acetylides in a heterogeneous process.