dc.contributor.author
Garg, Arushi
dc.contributor.author
Gerwien, Nils J.
dc.contributor.author
Fasting, Carlo
dc.contributor.author
Charlton, Alex
dc.contributor.author
Hopkinson, Matthew N.
dc.date.accessioned
2023-07-03T08:42:43Z
dc.date.available
2023-07-03T08:42:43Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/39697
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-39415
dc.description.abstract
C−F Insertion reactions represent an attractive approach to prepare valuable fluorinated compounds. The high strength of C−F bonds and the low reactivity of the fluoride released upon C−F bond cleavage, however, mean that examples of such processes are extremely scarce in the literature. Here we report a reaction system that overcomes these challenges using hydrogen bond donors that both activate C−F bonds and allow for downstream reactions with fluoride. In the presence of hexafluoroisopropanol, benzyl and propargyl fluorides undergo efficient formal C−F bond insertion across α-fluorinated styrenes. This process, which does not require any additional fluorinating reagent, occurs under mild conditions and delivers products featuring the gem-difluoro motif, which is attracting increasing interest in medicinal chemistry. Moreover, readily available organic bromides can be engaged directly in a one-pot process that avoids the isolation of organic fluorides.
en
dc.format.extent
7 Seiten
dc.rights.uri
https://creativecommons.org/licenses/by/4.0/
dc.subject
gem-Difluorinated Groups
en
dc.subject
Hydrogen Bonding
en
dc.subject
Insertion Reactions
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
Formal Insertion of Alkenes Into C(sp3)−F Bonds Mediated by Fluorine-Hydrogen Bonding
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation.articlenumber
e202302860
dcterms.bibliographicCitation.doi
10.1002/anie.202302860
dcterms.bibliographicCitation.journaltitle
Angewandte Chemie - International Edition
dcterms.bibliographicCitation.number
25
dcterms.bibliographicCitation.volume
62
dcterms.bibliographicCitation.url
https://doi.org/10.1002/anie.202302860
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Chemie und Biochemie
refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
dcterms.isPartOf.eissn
1521-3773
refubium.resourceType.provider
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