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Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
- 1.0474969 - ÚOCHB 2018 RIV DE eng J - Journal Article
Blastik, Zsófia E. - Voltrová, Svatava - Matoušek, V. - Jurásek, Bronislav - Manley, David W. - Klepetářová, Blanka - Beier, Petr
Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.
Angewandte Chemie - International Edition. Roč. 56, č. 1 (2017), s. 346-349. ISSN 1433-7851. E-ISSN 1521-3773
EU Projects: European Commission(XE) 607787 - FLUOR21
Institutional support: RVO:61388963
Keywords : azides * click reactions * fluorine * perfluoroalkanes * triazoles
OECD category: Organic chemistry
Impact factor: 12.102, year: 2017
http://onlinelibrary.wiley.com/doi/10.1002/anie.201609715/full
We report an efficient and scalable synthesis of azidotrifluoromethane (CF3N3) and longer perfluorocarbonchain analogues (RFN3, R-F= C2F5, (C3F7)-C-n, (C8F17)-C-n), 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.
Permanent Link: http://hdl.handle.net/11104/0271859
Number of the records: 1