Stable and Storable N(CF\(_{3}\))\(_{2}\) Transfer Reagents

Please always quote using this URN: urn:nbn:de:bvb:20-opus-256890
  • Fluorinated groups are essential for drug design, agrochemicals, and materials science. The bis(trifluoromethyl)amino group is an example of a stable group that has a high potential. While the number of molecules containing perfluoroalkyl, perfluoroalkoxy, and other fluorinated groups is steadily increasing, examples with the N(CF\(_{3}\))\(_{2}\) group are rare. One reason is that transfer reagents are scarce and metal-based storable reagents are unknown. Herein, a set of Cu\(^{I}\) and Ag\(^{I}\) bis(trifluoromethyl)amido complexes stabilizedFluorinated groups are essential for drug design, agrochemicals, and materials science. The bis(trifluoromethyl)amino group is an example of a stable group that has a high potential. While the number of molecules containing perfluoroalkyl, perfluoroalkoxy, and other fluorinated groups is steadily increasing, examples with the N(CF\(_{3}\))\(_{2}\) group are rare. One reason is that transfer reagents are scarce and metal-based storable reagents are unknown. Herein, a set of Cu\(^{I}\) and Ag\(^{I}\) bis(trifluoromethyl)amido complexes stabilized by N- and P-donor ligands with unprecedented stability are presented. The complexes are stable solids that can even be manipulated in air for a short time. They are bis(trifluoromethyl)amination reagents as shown by nucleophilic substitution and Sandmeyer reactions. In addition to a series of benzylbis(trifluoromethyl)amines, 2-bis(trifluoromethyl)amino acetate was obtained, which, upon hydrolysis, gives the fluorinated amino acid N,N-bis(trifluoromethyl)glycine.show moreshow less

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Metadaten
Author: Leon N. Schneider, Eva-Maria Tanzer Krauel, Carl Deutsch, Klaus Urbahns, Tobias Bischof, Kristina A. M. Maibom, Johannes Landmann, Fabian Keppner, Christoph Kerpen, Michael Hailmann, Ludwig Zapf, Tanja Knuplez, Rüdiger Bertermann, Nikolai V. Ignat'ev, Maik FinzeORCiD
URN:urn:nbn:de:bvb:20-opus-256890
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Language:English
Parent Title (English):Chemistry—A European Journal
Year of Completion:2021
Volume:27
Issue:42
Pagenumber:10973–10978
Source:Chemistry—A European Journal 2021, 27(42):10973–10978. DOI: 10.1002/chem.202101436
DOI:https://doi.org/10.1002/chem.202101436
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie
Tag:N ligands; amination; copper; fluorinated ligands; silver
Release Date:2022/03/08
Licence (German):License LogoCC BY-NC-ND: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell, Keine Bearbeitungen 4.0 International