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 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:	7
Deposited By:	Chemistry
Deposited On:	2019-08-13
Last Modified:	2019-12-09
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