Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition

Zsófia E Blastik; Svatava Voltrová; Václav Matoušek; Bronislav Jurásek; David W Manley; Blanka Klepetářová; Petr Beier

doi:10.1002/anie.201609715

Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition

Angew Chem Int Ed Engl. 2017 Jan 2;56(1):346-349. doi: 10.1002/anie.201609715. Epub 2016 Dec 5.

Authors

Zsófia E Blastik¹, Svatava Voltrová¹, Václav Matoušek², Bronislav Jurásek¹, David W Manley¹, Blanka Klepetářová¹, Petr Beier¹

Affiliations

¹ The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
² CF Plus Chemicals s.r.o., Kamenice 771/34, 625 00, Brno, Czech Republic.

PMID: 27918134
DOI: 10.1002/anie.201609715

Abstract

We report an efficient and scalable synthesis of azidotrifluoromethane (CF₃ N₃ ) and longer perfluorocarbon-chain analogues (R_F N₃ ; R_F =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.

Keywords: azides; click reactions; fluorine; perfluoroalkanes; triazoles.

Publication types

Research Support, Non-U.S. Gov't