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Proton supplier role of binuclear gold complexes in promoting hydrofunctionalisation of nonactivated alkenes

Citation

Asgari, M and Hyland, CJT and Hashmi, ASK and Yates, BF and Ariafard, A, Proton supplier role of binuclear gold complexes in promoting hydrofunctionalisation of nonactivated alkenes, Catalysis Science & Technology, 9 pp. 1420-1426. ISSN 2044-4753 (2019) [Refereed Article]

Copyright Statement

The Royal Society of Chemistry 2019

DOI: doi:10.1039/c8cy02482k

Abstract

Density functional theory (DFT) was used to investigate PR3AuOTf-catalyzed hydrofunctionalisation of nonactivated alkenes using acetic acid and phenol where OTf = triflate (CF3SO3). The gold(I) complex itself is found to be unlikely to operate as the π-activator due to its relatively low electrophilicity. Instead, the concurrent coordination of two gold(I) complexes to a nucleophile (PhOH or AcOH) enhances the acidity of the latter's proton and causes the ensuing binuclear complex to serve as a strong proton supplier for activating the alkene π-bonds. Alternatively, the binuclear complex is also susceptible to produce a hidden HOTf. This hidden acid is accessible for hydrofunctionalization to occur but it is not in sufficient concentration to decompose the final product.

Item Details

Item Type:Refereed Article
Keywords:density functional theory, activation energy
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Physical Organic Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
UTAS Author:Yates, BF (Professor Brian Yates)
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:134443
Year Published:2019
Funding Support:Australian Research Council (DP180100904)
Web of Science® Times Cited:3
Deposited By:Chemistry
Deposited On:2019-08-13
Last Modified:2019-12-09
Downloads:0

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