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Unsupported Copper Nanoparticles in the 1,3‐Dipolar Cycloaddition of Terminal Alkynes and Azides
Author(s) -
Alonso Francisco,
Moglie Yanina,
Radivoy Gabriel,
Yus Miguel
Publication year - 2010
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.200901446
Subject(s) - chemistry , cycloaddition , copper , reactivity (psychology) , 1,3 dipolar cycloaddition , click chemistry , nanoparticle , combinatorial chemistry , ligand (biochemistry) , reaction mechanism , organic chemistry , photochemistry , catalysis , nanotechnology , materials science , medicine , biochemistry , alternative medicine , receptor , pathology
Readily prepared copper nanoparticles were found to catalyse the 1,3‐dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3‐triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.