Pentafluoro(aryl)-λ
fluorine chemistry
oxidative fluorination
structure elucidation
tellurium
trichloroisocyanuric acid
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
02 09 2019
02 09 2019
Historique:
received:
13
06
2019
pubmed:
30
6
2019
medline:
30
6
2019
entrez:
29
6
2019
Statut:
ppublish
Résumé
The TeF
Identifiants
pubmed: 31250962
doi: 10.1002/anie.201907359
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
12604-12608Subventions
Organisme : Eidgenössische Technische Hochschule Zürich
Pays : International
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 200020_175487
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
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More recently, we also reported an application of this TCICA/KF oxidative fluorination approach to aryl iodides in the synthesis of aryl-IF2 and aryl-IF4 compounds. See: J. Häfliger, C. R. Pitts, D. Bornemann, R. Käser, N. Santschi, J. Charpentier, E. Otth, N. Trapp, R. Verel, H. P. Lüthi, A. Togni, Chem. Sci. 2019, 10, 7251-7259.
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Another interesting comparison to the arene-based TeF4CF3 group is the corresponding SF4CF3 group, for instance, see: P. Kirsch, A. Hahn, Eur. J. Org. Chem. 2006, 1125-1131.
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The molecular structures for benzophenone, 4-(trifluoromethyl)benzophenone, and 4-(pentafluorosulfanyl)benzophenone used in this comparative analysis were previously reported, and have CCDC deposition numbers of 1114983, 1005255, and 1865801, respectively.
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For instance, after 36 h, Ph-TeF2(OH)2(CF3)-the putative dihydrolysis product-was observed as the major species: 19F NMR (282 MHz, CD3CN): −59.97 (3F, t, J=16.6 Hz), −72.16 (2F, q, J=16.6 Hz).
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CCDC 1922277 (4), 1922269 (5), 1922276 (7), 1922270 (9), 1922271 (10), 1922275 (11), 1922278 (14), 1922272 (15), and 1922274 (17) contain the supplementary crystallographic data for this paper. These data are provided free of charge by Cambridge Crystallographic Data Centre.