Synthesis of tetrafluoroethylene- and tetrafluoroethyl-containing azides and their 1,3-dipolar cycloaddition as synthetic application

Svatava Voltrová; Mickaël Muselli; Josef Filgas; Václav Matoušek; Blanka Klepetářová; Petr Beier

doi:10.1039/c7ob01151b

Synthesis of tetrafluoroethylene- and tetrafluoroethyl-containing azides and their 1,3-dipolar cycloaddition as synthetic application

Org Biomol Chem. 2017 Jun 14;15(23):4962-4965. doi: 10.1039/c7ob01151b.

Authors

Svatava Voltrová¹, Mickaël Muselli¹, Josef Filgas¹, Václav Matoušek², Blanka Klepetářová¹, Petr Beier¹

Affiliations

¹ The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague, Czech Republic. beier@uochb.cas.cz.
² CF Plus Chemicals s.r.o., Kamenice 771/34, 625 00 Brno, Czech Republic.

PMID: 28548159
DOI: 10.1039/c7ob01151b

Abstract

Tetrafluoroethylene-containing azides are accessed in two steps (one pot) from tetrafluoroalkyl bromides by metalation and reaction with electrophilic azides. Subsequent copper(i)-catalyzed azide-alkyne cycloaddition afforded N-tetrafluoroethyl and N-tetrafluoroethylene 4-substituted 1,2,3-triazoles. In addition, the protocol for the synthesis of 4,5-disubstituted 1,2,3-triazoles is presented.