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Stable and Storable N(CF 3 ) 2 Transfer Reagents
Author(s) -
Schneider Leon N.,
Tanzer Krauel EvaMaria,
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
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101436
Subject(s) - trifluoromethyl , chemistry , reagent , amination , nucleophile , hydrolysis , nucleophilic substitution , molecule , medicinal chemistry , intermolecular force , organic chemistry , combinatorial chemistry , catalysis , alkyl
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.