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Issue 27, 2015
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Anomalous ligand effect in gold(i)-catalyzed intramolecular hydroamination of alkynes

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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.

Graphical abstract: Anomalous ligand effect in gold(i)-catalyzed intramolecular hydroamination of alkynes

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Article information


Submitted
03 Feb 2015
Accepted
23 Feb 2015
First published
23 Feb 2015

Chem. Commun., 2015,51, 5990-5993
Article type
Communication
Author version available

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

C. A. Gaggioli, G. Ciancaleoni, L. Biasiolo, G. Bistoni, D. Zuccaccia, L. Belpassi, P. Belanzoni and F. Tarantelli, Chem. Commun., 2015, 51, 5990
DOI: 10.1039/C5CC00894H

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