Journal
DALTON TRANSACTIONS
Volume 44, Issue 33, Pages 14747-14752Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5dt02405f
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Funding
- Petroleum Research Fund [51715-ND3]
- US Department of Energy, Materials Sciences Division [DE-SC0010510]
- UF
- NSF [CHE-0821346]
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This report outlines the investigation of the iClick mechanism between gold(I)-azides and gold(I)-acetylides to yield digold triazolates. Isolation of digold triazolate complexes offer compelling support for the role of two copper(I) ions in CuAAC. In addition, a kinetic investigation reveals the reaction is first order in both Au(I)-N-3 and Au(I)-Cu equivalent to C-R, thus second order overall. A Hammett plot with a rho = 1.02(5) signifies electron-withdrawing groups accelerate the cycloaddition by facilitating the coordination of the second gold ion in a pi-complex. Rate inhibition by the addition of free triphenylphosphine to the reaction indicates that ligand dissociation is a prerequisite for the reaction. The mechanistic conclusions mirror those proposed for the CuAAC reaction.
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