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Photochemical activation of a hydroxyquinone-derived phenyliodonium ylide by visible light: synthetic and mechanistic investigations

Citation

Jalali, M and Ho, CC and Fuller, RO and Lucas, NT and Ariafard, A and Bissember, AC, Photochemical activation of a hydroxyquinone-derived phenyliodonium ylide by visible light: synthetic and mechanistic investigations, Journal of Organic Chemistry, 86, (2) pp. 1758-1768. ISSN 0022-3263 (2021) [Refereed Article]

Copyright Statement

Copyright 2020 American Chemical Society

DOI: doi:10.1021/acs.joc.0c02592

Abstract

We have identified and extensively investigated the photochemical activation and reaction of a hydroxyquinone-derived phenyliodonium ylide in the presence of visible light using experiment and theory. These studies revealed that in its photoexcited state this iodonium is capable of facilitating a range of single-electron transfer (SET) processes, including hydrogen atom transfer (HAT), a Povarov-type reaction, and atom-transfer radical addition chemistry. Where possible, we have employed density functional theory (DFT) to develop a more complete understanding of these photoinduced synthetic transformations.

Item Details

Item Type:Refereed Article
Keywords:hypervalent iodine, radical chemistry, photochemistry
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Jalali, M (Mr Mohammad Jalali)
UTAS Author:Ho, CC (Dr Curtis Ho)
UTAS Author:Fuller, RO (Dr Rebecca Fuller)
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
UTAS Author:Bissember, AC (Associate Professor Alex Bissember)
ID Code:142423
Year Published:2021
Funding Support:Australian Research Council (DP200101714)
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2021-01-16
Last Modified:2021-04-14
Downloads:0

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