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

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

doi:10.1002/ange.201609715

Angewandte Chemie

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

Authors

Zsófia E. Blastik,
1. The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Prague 6, Czech Republic
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Dr. Svatava Voltrová,
1. The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Prague 6, Czech Republic
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Dr. Václav Matoušek,
1. CF Plus Chemicals s.r.o., Brno, Czech Republic
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Bronislav Jurásek,
1. The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Prague 6, Czech Republic
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Dr. David W. Manley,
1. The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Prague 6, Czech Republic
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Dr. Blanka Klepetářová,
1. The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Prague 6, Czech Republic
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Dr. Petr Beier
Corresponding author
- E-mail address: beier@uochb.cas.cz
- ORCID:orcid.org/0000-0002-0888-7465
1. The Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Prague 6, Czech Republic
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First published: 5 December 2016Full publication history
DOI: 10.1002/ange.201609715 View/save citation
Cited by (CrossRef): 0 articles Check for updates
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Abstract

We report an efficient and scalable synthesis of azidotrifluoromethane (CF₃N₃) and longer perfluorocarbon-chain analogues (R_FN₃; R_F=C₂F₅, ⁿC₃F₇, ⁿC₈F₁₇), 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.

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DOI

10.1002/ange.201609715

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Keywords

Azide;
Fluor;
Klick-Reaktionen;
Perfluoralkane;
Triazole

Publication History

Issue online: 28 December 2016
Version of record online: 5 December 2016
Manuscript Received: 4 October 2016

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