Azidoperfluoroalkanes: Synthesis and Application in Copper(I)‐Catalyzed Azide–Alkyne Cycloaddition. Issue 1 (5th December 2016)

• Record Type: Journal Article
• Authors: Blastik, Zsófia E.; Voltrová, Svatava; Matoušek, Václav; Jurásek, Bronislav; Manley, David W.; Klepetářová, Blanka; Beier, Petr
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 1(2017)
• Page Start: 346
• Page End: 349
• Publication Date: 2016-12-05
• Subjects: azides -- click reactions -- fluorine -- perfluoroalkanes -- triazoles; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201609715
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report an efficient and scalable synthesis of azidotrifluoromethane (CF3 N3 ) and longer perfluorocarbon‐chain analogues (RF N3 ; RF =C2 F5, n C3 F7, n C8 F17 ), 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. Abstract : No longer chemical curiosities : Azidoperfluoroalkanes were conveniently prepared from perfluoroalkyl carbanion precursors and electrophilic azide reagents. The azidoperfluoroalkanes show good stability and good reactivity with terminal alkynes in copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC), giving access to rare and stable N ‐perfluoroalkyl triazoles.