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Issue 2, 2010
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Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes

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Abstract

Alkylgold(I) complexes were formed from the gold(I)-promoted intramolecular addition of various amine nucleophiles to alkenes. These experiments provide the first direct experimental evidence for the elementary step of gold-promoted nucleophilic addition to an alkene. Deuterium-labeling studies and X-ray crystal structures provide support for a mechanism involving anti-addition of the nucleophile to a gold-activated alkene, which is verified by DFT analysis of the mechanism. Ligand studies indicate that the rate of aminoauration can be drastically increased by use of electron-poor arylphosphines, which are also shown to be favored in ligand exchange experiments. Attempts at protodeauration lead only to recovery of the starting olefins, though the gold can be removed under reducing conditions to provide the purported hydroamination products.

Graphical abstract: Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes

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Supplementary files

Article information


Submitted
06 Apr 2010
Accepted
05 May 2010
First published
10 Jun 2010

Chem. Sci., 2010,1, 226-233
Article type
Edge Article

Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes

R. L. LaLonde, W. E. Brenzovich, Jr., D. Benitez, E. Tkatchouk, K. Kelley, W. A. Goddard, III and F. D. Toste, Chem. Sci., 2010, 1, 226
DOI: 10.1039/C0SC00255K

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