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

Citation

Bagi, AH and Khaledi, Y and Ghari, H and Arndt, S and Hashmi, AS and Yates, BF and Ariafard, A, A Mechanistic Investigation of the Gold(III)-Catalyzed Hydrofurylation of C-C Multiple Bonds, Journal of the American Chemical Society, 138, (44) pp. 14599-14608. ISSN 0002-7863 (2016) [Refereed Article]

Copyright Statement

2016 American Chemical Society

DOI: doi:10.1021/jacs.6b05742

Abstract

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.

Item Details

Item Type:Refereed Article
Keywords:gold catalysis
Research Division:Chemical Sciences
Research Group:Physical Chemistry (incl. Structural)
Research Field:Catalysis and Mechanisms of Reactions
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Yates, BF (Professor Brian Yates)
Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:114972
Year Published:2016
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2017-03-03
Last Modified:2017-05-19
Downloads:0

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