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dc.contributor.author
Zhang, Kun
dc.contributor.author
Rombach, David
dc.contributor.author
Notel, Nicolas Yannick
dc.contributor.author
Jeschke, Gunnar
dc.contributor.author
Katayev, Dmitry
dc.date.accessioned
2021-10-08T07:49:17Z
dc.date.available
2021-09-15T02:46:19Z
dc.date.available
2021-10-08T07:49:17Z
dc.date.issued
2021
dc.identifier.issn
1433-7851
dc.identifier.issn
1521-3773
dc.identifier.issn
0570-0833
dc.identifier.other
10.1002/anie.202109235
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/505548
dc.identifier.doi
10.3929/ethz-b-000505548
dc.description.abstract
We report a mild and operationally simple trifluoroacylation strategy of olefines, that utilizes trifluoroacetic anhydride as a low-cost and readily available reagent. This light-mediated process is fundamentally different from conventional methodologies and occurs through a trifluoroacyl radical mechanism promoted by a photocatalyst, which triggers a C-O bond fragmentation. Mechanistic studies (kinetic isotope effects, spectroelectrochemistry, optical spectroscopy, theoretical investigations) highlight the evidence of a fleeting CF3CO radical under photoredox conditions. The trifluoroacyl radical can be stabilized under CO atmosphere, delivering the trifluoroacetylation product with higher chemical efficiency. Furthermore, the method can be turned into a trifluoromethylation protocol by simply changing the reaction parameters. Beyond simple alkenes, this method allows for chemo- and regioselective functionalization of small-molecule drugs and common pharmacophores.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Wiley-VCH
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc/4.0/
dc.subject
late-stage functionalization
en_US
dc.subject
organofluorine compounds
en_US
dc.subject
photoredox
en_US
dc.subject
radical mechanisms
en_US
dc.subject
radical trifluoroacetylation
en_US
dc.title
Radical Trifluoroacetylation of Alkenes Triggered by a Visible-Light-Promoted C-O Bond Fragmentation of Trifluoroacetic Anhydride
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial 4.0 International
dc.date.published
2021-07-21
ethz.journal.title
Angewandte Chemie. International Edition
ethz.journal.volume
60
en_US
ethz.journal.issue
41
en_US
ethz.journal.abbreviated
Angew. Chem. Int. Ed.
ethz.pages.start
22487
en_US
ethz.pages.end
22495
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Weinheim
en_US
ethz.publication.status
published
en_US
ethz.date.deposited
2021-09-15T02:46:28Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2022-01-31T14:53:50Z
ethz.rosetta.lastUpdated
2022-01-31T14:53:50Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
ethz.COinS
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