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A Mechanistic Investigation of the Gold(III)-Catalyzed Hydrofurylation of C-C Multiple Bonds

journal contribution
posted on 2023-05-19, 02:48 authored by Bagi, AH, Khaledi, Y, Ghari, H, Arndt, S, Hashmi, ASK, Brian YatesBrian Yates, Alireza AriafardAlireza Ariafard
The reaction mechanism of the gold(I)-phosphine-catalyzed addition of phenols to olefins was analyzed by means of theoretical methods combined with polarizable continuum models. Several mechanistic pathways for the reaction were considered and evaluated. The most favorable one includes the ligand substitution of triflate by the alkene in the catalytically active R3PAuOTf species and subsequent nucleophile attack of phenol on the activated double bond concomitantly with the proton transfer from the OH group to the other carbon atom. The energy barrier for this concerted transition state diminishes dramatically when a proton transfer agent is present. These species are acting as proton shuttles in the proton transfer step. Noteworthy, the proton transfer in the phenol addition, both for the PhOH- or H2O-assisted processes, is a concerted step.

History

Publication title

Journal of the American Chemical Society

Volume

138

Issue

44

Pagination

14599-14608

ISSN

0002-7863

Department/School

School of Natural Sciences

Publisher

American Chemical Society

Place of publication

United States

Rights statement

© 2016 American Chemical Society

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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