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Stable and Storable N(CF\(_{3}\))\(_{2}\) Transfer Reagents (2021)
Schneider, Leon N. ; Tanzer Krauel, Eva-Maria ; Deutsch, Carl ; Urbahns, Klaus ; Bischof, Tobias ; Maibom, Kristina A. M. ; Landmann, Johannes ; Keppner, Fabian ; Kerpen, Christoph ; Hailmann, Michael ; Zapf, Ludwig ; Knuplez, Tanja ; Bertermann, Rüdiger ; Ignat'ev, Nikolai V. ; Finze, Maik
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 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.
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