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

作者：Blastik Zsofia E; Voltrova Svatava; Matousek Vaclav; Jurasek Bronislav; Manley David W; Klepetarova Blanka; Beier Petr

来源：Angewandte Chemie - International Edition, 2017, 56(1): 346-349.

DOI：10.1002/anie.201609715

<jats:title>Abstract</jats:title><jats:p>We report an efficient and scalable synthesis of azidotrifluoromethane (CF<jats:sub>3</jats:sub>N<jats:sub>3</jats:sub>) and longer perfluorocarbon‐chain analogues (R<jats:sub>F</jats:sub>N<jats:sub>3</jats:sub>; R<jats:sub>F</jats:sub>=C<jats:sub>2</jats:sub>F<jats:sub>5</jats:sub>, <jats:sup><jats:italic>n</jats:italic></jats:sup>C<jats:sub>3</jats:sub>F<jats:sub>7</jats:sub>, <jats:sup><jats:italic>n</jats:italic></jats:sup>C<jats:sub>8</jats:sub>F<jats:sub>17</jats:sub>), which enables the direct insertion of CF<jats:sub>3</jats:sub> 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 <jats:italic>N</jats:italic>‐perfluoroalkyl triazoles. Azidoperfluoroalkanes are thermally stable and the efficiency of their preparation should be attractive for discovery programs.</jats:p>

• 出版日期2017-1-2