Issue 6, 2019
From the journal:

Catalysis Science & Technology

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

Maryam Asgari,a   Christopher J. T. Hyland, ORCID logo b   A. Stephen K. Hashmi, ORCID logo c   Brian F. Yates ORCID logo d  and  Alireza Ariafard ORCID logo *ad  

* Corresponding authors

a Department of Chemistry, Central Tehran Branch, Islamic Azad University, Poonak, Tehran, Iran

b School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia

c Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

d School of Natural Sciences (Chemistry), University of Tasmania, Private Bag 75, Hobart TAS 7001, Australia
E-mail: Alireza.Ariafard@utas.edu.au

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.

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

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Article information

DOI
https://doi.org/10.1039/C8CY02482K
Article type
Paper
Submitted
09 Dec 2018
Accepted
21 Feb 2019
First published
21 Feb 2019

Catal. Sci. Technol., 2019,9, 1420-1426

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

M. Asgari, C. J. T. Hyland, A. S. K. Hashmi, B. F. Yates and A. Ariafard, Catal. Sci. Technol., 2019, 9, 1420 DOI: 10.1039/C8CY02482K

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