Anomalous ligand effect in gold(I)-catalyzed intramolecular hydroamination of 
alkynes

Gaggioli, Carlo Alberto; Ciancaleoni, Gianluca; Biasiolo, Luca; Bistoni, Giovanni; Zuccaccia, Daniele; Belpassi, Leonardo; Belanzoni, Paola; Tarantelli, Francesco

doi:10.1039/C5CC00894H

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Anomalous ligand effect in gold(I)-catalyzed intramolecular hydroamination of alkynes

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Gaggioli, C. A., Ciancaleoni, G., Biasiolo, L., Bistoni, G., Zuccaccia, D., Belpassi, L., et al. (2015). Anomalous ligand effect in gold(I)-catalyzed intramolecular hydroamination of alkynes. Chemical Communications, 51(27), 5990-5993. doi:10.1039/C5CC00894H.

Cite as: https://hdl.handle.net/21.11116/0000-0008-705D-2

Abstract

We analyzed the ligand electronic effect in a gold(I)-catalyzed intramolecular alkyne hydroamination, through a DFT and charge-displacement function (CDF) study. We found that, in the presence of π-electron conjugation between the alkyne and the nucleophilic functionality, electron poor ligands modify the coordination mode and the geometric parameters of the substrate in such a way that, contrary to expectations, the activation barrier of the nucleophilic attack increases. This remarkable effect is due to the competition between alkyne activation and nucleophile deactivation. The general relevance of these findings is highlighted.