Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation

Balázs L. Tóth, Szabolcs Kovács, Gergo a. Sályi, Z. Novák

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95% yield at 25°C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2016

Keywords

  • Anilides
  • C-H activation
  • Iodonium salts
  • Palladium
  • Trifluoroethylation

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Fingerprint Dive into the research topics of 'Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation'. Together they form a unique fingerprint.

  • Cite this