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Article Dans Une Revue Computational and Theoretical Chemistry Année : 2015

Reaction Mechanisms of Transition-Metal-Catalyzed Azide-Alkyne Cycloaddition “Click” Reactions: A DFT Investigation

Résumé

DFT calculations at the PBE0/LANL2DZ level have been performed on model compounds to investigate the reaction mechanism of two recently reported metal-catalyzed alkyne azide cycloaddition (MAAC). The first one, that involves a [Cu(tren)]+Br- catalyst, is shown not to proceed through a metal alkynyl intermediate, but, after precomplexation of the alkyne in an η2-mode, directly to the 1,4-disubstituted 1,2,3-triazole product, through a metallacyclic transition state. The other system, involving a rare-earth Ln[N(SiMe3)2]3 complex, is found to proceed through an alkynyl-azide complex which produces an η 2-coordinated heterocyclic ligand before protonation by an incoming alkyne molecule. Our results are discussed with respect to other computational data from the literature
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Dates et versions

hal-01208404 , version 1 (03-12-2015)

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Djamila Ikhlef, Changlong Wang, Samia Kahlal, Boubekeur Maouche, Didier Astruc, et al.. Reaction Mechanisms of Transition-Metal-Catalyzed Azide-Alkyne Cycloaddition “Click” Reactions: A DFT Investigation. Computational and Theoretical Chemistry, 2015, 1073, pp.131-138. ⟨10.1016/j.comptc.2015.09.020⟩. ⟨hal-01208404⟩
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