Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom Transfer Article Swipe
Joshua L. Zhu
,
Cullen R. Schull
,
Anthony T. Tam
,
Ángel Rentería‐Gómez
,
Achyut Ranjan Gogoi
,
Osvaldo Gutiérrez
,
Karl A. Scheidt
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.2c12845
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.2c12845
Photoinduced hydrogen atom transfer (HAT) has been developed as a powerful tool to generate synthetically valuable radical species. The direct photoexcitation of ketones has been known to promote HAT or to generate acyl radicals through Norrish-type pathways, but these modalities remain severely limited by radical side reactions. We report herein a catalyst- and transition metal-free method for the acylation of C-H bonds that leverages the unique properties of stable, isolable acyl azolium species. Specifically, acyl azolium salts are shown to undergo an intermolecular and regioselective HAT upon LED irradiation with a range of substrates bearing active C-H bonds followed by C-C bond formation to afford ketones. Experimental and computational studies support photoexcitation of the acyl azolium followed by facile intersystem crossing to access triplet diradical species that promote selective HAT and radical-radical cross-coupling.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/jacs.2c12845
- OA Status
- green
- Cited By
- 70
- References
- 73
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4313946435
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4313946435Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/jacs.2c12845Digital Object Identifier
- Title
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Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom TransferWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2023Year of publication
- Publication date
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2023-01-10Full publication date if available
- Authors
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Joshua L. Zhu, Cullen R. Schull, Anthony T. Tam, Ángel Rentería‐Gómez, Achyut Ranjan Gogoi, Osvaldo Gutiérrez, Karl A. ScheidtList of authors in order
- Landing page
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https://doi.org/10.1021/jacs.2c12845Publisher landing page
- Open access
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YesWhether a free full text is available
- OA status
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greenOpen access status per OpenAlex
- OA URL
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https://pmc.ncbi.nlm.nih.gov/articles/PMC10191224/pdf/nihms-1892516.pdfDirect OA link when available
- Concepts
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Chemistry, Intermolecular force, Hydrogen atom, Atom (system on chip), Photochemistry, Hydrogen bond, Molecule, Organic chemistry, Group (periodic table), Computer science, Embedded systemTop concepts (fields/topics) attached by OpenAlex
- Cited by
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70Total citation count in OpenAlex
- Citations by year (recent)
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2025: 20, 2024: 25, 2023: 25Per-year citation counts (last 5 years)
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73Number of works referenced by this work
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-
10Other works algorithmically related by OpenAlex
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