Photochemical Activation of a Hydroxyquinone-Derived Phenyliodonium Ylide by Visible Light: Synthetic and Mechanistic Investigations

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 ra...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-01, Vol.86 (2), p.1758-1768
Main Authors: Jalali, Mona, Ho, Curtis C, Fuller, Rebecca O, Lucas, Nigel T, Ariafard, Alireza, Bissember, Alex C
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02592