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

Jalali, M, Ho, CC ORCID: 0000-0002-7555-0635, Fuller, RO ORCID: 0000-0003-3926-8680, Lucas, NT, Ariafard, A ORCID: 0000-0003-2383-6380 and Bissember, AC ORCID: 0000-0001-5515-2878 2021 , 'Photochemical activation of a hydroxyquinone-derived phenyliodonium ylide by visible light: synthetic and mechanistic investigations' , Journal of Organic Chemistry, vol. 86, no. 2 , pp. 1758-1768 , doi: 10.1021/acs.joc.0c02592.

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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 Type: Article
Authors/Creators:Jalali, M and Ho, CC and Fuller, RO and Lucas, NT and Ariafard, A and Bissember, AC
Keywords: hypervalent iodine, radical chemistry, photochemistry
Journal or Publication Title: Journal of Organic Chemistry
Publisher: Amer Chemical Soc
ISSN: 0022-3263
DOI / ID Number: 10.1021/acs.joc.0c02592
Copyright Information:

Copyright 2020 American Chemical Society

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