Competitive gold-activation modes in terminal alkynes: An experimental and mechanistic study

Ana Gimeno, Ana B. Cuenca, Samuel Suárez-Pantiga, Carmen Ramírez De Arellano, Mercedes Medio-Simõn, Gregorio Asensio

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The competition between π- and dual σ,π-gold-activation modes is revealed in the gold(I)-catalyzed heterocyclization of 1-(o-ethynylaryl)urea. A noticeable effect of various ligands in gold complexes on the choice of these activation modes is described. The cationic [Au(IPr)]+ (IPr=2,6-bis(diisopropylphenyl)imidazol-2-ylidene) complex cleanly promotes the π activation of terminal alkynes, whereas [Au(PtBu3)]+ favors intermediate σ,π species. In this experimental and mechanistic study, which includes kinetic and cross-over experiments, several σ-gold, σ,π-gold, and other gold polynuclear reaction intermediates have been isolated and identified by NMR spectroscopy, X-ray diffraction, or MALDI spectrometry. The ligand control in the simultaneous or alternative π- and σ,π-activation modes is also supported by deuterium-labeling experiments.

Idioma originalAnglès
Pàgines (de-a)683-688
Nombre de pàgines6
RevistaChemistry - A European Journal
Estat de la publicacióPublicada - 13 de gen. 2014
Publicat externament


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