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Azidoperfluoroalkanes: Synthesis and Application in Copper(I)‐Catalyzed Azide–Alkyne Cycloaddition
Author(s) -
Blastik Zsófia E.,
Voltrová Svatava,
Matoušek Václav,
Jurásek Bronislav,
Manley David W.,
Klepetářová Blanka,
Beier Petr
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609715
Subject(s) - cycloaddition , alkyne , azide , chemistry , catalysis , combinatorial chemistry , copper , reactivity (psychology) , ring (chemistry) , triazole , medicinal chemistry , stereochemistry , organic chemistry , medicine , alternative medicine , pathology
We report an efficient and scalable synthesis of azidotrifluoromethane (CF 3 N 3 ) and longer perfluorocarbon‐chain analogues (R F N 3 ; R F =C 2 F 5 , n C 3 F 7 , n C 8 F 17 ), which enables the direct insertion of CF 3 and perfluoroalkyl groups into triazole ring systems. The azidoperfluoroalkanes show good reactivity with terminal alkynes in copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC), giving access to rare and stable N ‐perfluoroalkyl triazoles. Azidoperfluoroalkanes are thermally stable and the efficiency of their preparation should be attractive for discovery programs.