Heterogeneous Platinum-Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes

Fluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple proto...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2015-03, Vol.54 (14), p.4320-4324
Main Authors: He, Lin, Natte, Kishore, Rabeah, Jabor, Taeschler, Christoph, Neumann, Helfried, Brückner, Angelika, Beller, Matthias
Format: Article
Language:English
Subjects:
Aromatic compounds
Availability
Catalysts
CH activation
Economics
heterogeneous catalysis
Perfluoroalkyls
Platinum
Radicals
Synthesis
synthetic methods
Tolerances
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Summary:Fluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple protocol for the direct CH perfluoroalkylation of (hetero)arenes with RfI or RfBr has been developed, using a robust supported platinum catalyst. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of the catalyst make this method attractive for the synthesis of a variety of perfluoroalkyl‐substituted aromatic compounds. Preliminary mechanistic studies revealed the formation of radicals to be crucial in the reaction system. Platinum level: The efficient and versatile title reaction is based on the radical reactivity of perfluoroalkyl halides. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of catalyst make this protocol attractive for the economic synthesis of perfluoroalkyl‐group‐substituted aromatic compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201411066