title: Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.
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 CF3and 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.
authors.affiliation: The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
authors.forename: Zsófia E
authors.initials: ZE
authors.lastname: Blastik
authors.affiliation: The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
authors.forename: Svatava
authors.initials: S
authors.lastname: Voltrová
authors.affiliation: CF Plus Chemicals s.r.o., Kamenice 771/34, 625 00, Brno, Czech Republic.
authors.forename: Václav
authors.initials: V
authors.lastname: Matoušek
authors.affiliation: The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
authors.forename: Bronislav
authors.initials: B
authors.lastname: Jurásek
authors.affiliation: The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
authors.forename: David W
authors.initials: DW
authors.lastname: Manley
authors.affiliation: The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
authors.forename: Blanka
authors.initials: B
authors.lastname: Klepetářová
authors.affiliation: The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
authors.forename: Petr
authors.identifier: 0000-0002-0888-7465
authors.initials: P
authors.lastname: Beier
keywords: azides; click reactions; fluorine; perfluoroalkanes; triazoles