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Proton supplier role of binuclear gold complexes in promoting hydrofunctionalisation of nonactivated alkenes
journal contribution
posted on 2023-05-20, 06:18 authored by Asgari, M, Hyland, CJT, Hashmi, ASK, Brian YatesBrian Yates, Alireza AriafardAlireza AriafardDensity 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.
Funding
Australian Research Council
University of Wollongong
History
Publication title
Catalysis Science & TechnologyVolume
9Pagination
1420-1426ISSN
2044-4753Department/School
School of Natural SciencesPublisher
Royal Society of ChemistryPlace of publication
UKRights statement
© The Royal Society of Chemistry 2019Repository Status
- Restricted