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- Title
Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.
- Authors
Blastik, Zsófia E.; Voltrová, Svatava; Matoušek, Václav; Jurásek, Bronislav; Manley, David W.; Klepetářová, Blanka; Beier, Petr
- Abstract
We report an efficient and scalable synthesis of azidotrifluoromethane (CF3N3) and longer perfluorocarbon-chain analogues (RFN3; RF=C2F5, nC3F7, nC8F17), which enables the direct insertion of CF3 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.
- Subjects
FLUOROMETHANE; PERFLUOROCARBONS; TRIAZOLES; ALKYNES; AZIDES
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 1, p346
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201609715