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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
2021-09-15T02:46:19Z
dc.date.available
2021-09-15T02:46:19Z
dc.date.issued
2021-09-07
dc.identifier.issn
1433-7851
dc.identifier.issn
1521-3773
dc.identifier.issn
0570-0833
dc.identifier.other
10.1002/anie.202109235
dc.identifier.uri
http://hdl.handle.net/20.500.11850/505548
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.
dc.publisher
WILEY-V C H VERLAG GMBH
dc.subject
late-stage functionalization
dc.subject
organofluorine compounds
dc.subject
photoredox
dc.subject
radical mechanisms
dc.subject
radical trifluoroacetylation
dc.title
Radical Trifluoroacetylation of Alkenes Triggered by a Visible-Light-Promoted C-O Bond Fragmentation of Trifluoroacetic Anhydride
dc.type
Journal Article
ethz.journal.title
Angewandte Chemie. International Edition
ethz.journal.abbreviated
Angew. Chem. Int. Ed.
ethz.identifier.wos
ethz.publication.place
WEINHEIM
ethz.date.deposited
2021-09-15T02:46:28Z
ethz.source
WOS
ethz.rosetta.exportRequired
true
ethz.COinS
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