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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 |
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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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