Heterogeneous platinum-catalyzed C-H perfluoroalkylation of arenes and heteroarenes

Lin He, Kishore Natte, Jabor Rabeah, Christoph Taeschler, Helfried Neumann, Angelika Brückner, Matthias Beller

Research output: Contribution to journalArticlepeer-review

77 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)4320-4324
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume54
Issue number14
DOIs
StatePublished - 27 Mar 2015
Externally publishedYes

Keywords

  • C-H activation
  • heterogeneous catalysis
  • platinum
  • radicals
  • synthetic methods

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