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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 Ariafard
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.

Funding

Australian Research Council

University of Wollongong

History

Publication title

Catalysis Science & Technology

Volume

9

Pagination

1420-1426

ISSN

2044-4753

Department/School

School of Natural Sciences

Publisher

Royal Society of Chemistry

Place of publication

UK

Rights statement

© The Royal Society of Chemistry 2019

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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