Palladium-Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br

Kishore Natte, Rajenahally V. Jagadeesh, Lin He, Jabor Rabeah, Jianbin Chen, Christoph Taeschler, Stefan Ellinger, Florencio Zaragoza, Helfried Neumann, Angelika Brückner, Matthias Beller

Research output: Contribution to journalArticlepeer-review

112 Scopus citations

Abstract

The CF3 group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well-established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl-substituted (hetero)arenes by palladium-catalyzed C-H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio- and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased.

Original languageEnglish
Pages (from-to)2782-2786
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume55
Issue number8
DOIs
StatePublished - 18 Feb 2016
Externally publishedYes

Keywords

  • C-H activation
  • arenes
  • fluorine
  • palladium
  • radical chemistry

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