Expedient Trifluoromethylacylation of Styrenes Enabled by Photoredox Catalysis

Lu Wang, Heng Zhang, Chuan Zhu, Chao Feng

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Herein, we disclosed a photoredox enabled protocol for trifluoromethylacylation of styrenes through a radical-carboanion cascade and subsequent oxidation. With a broad range of aldehydes and inexpensive Langlois reagent as acyl and CF3 precursor, respectively, the alkene motif could be readily converted into β-trifluoromethyl ketones in moderate to good yields and with excellent regioselectivity. Besides CF3, di-, mono- and non-fluorinated C-radicals were revealed amenable in this reaction, providing good opportunity for the construction of structurally diverse ketones of interest in pharmaceutical research. Additionally, the utility of this protocol was further demonstrated by successful extension to trifluoromethylarylation and -alkylation by employing arylcyanide or acrylates in place of carbonyls.

Original languageEnglish
Pages (from-to)59-64
Number of pages6
JournalChinese Journal of Chemistry
Volume40
Issue number1
DOIs
StatePublished - Jan 2022

Keywords

  • Alkenes
  • CF radical
  • Photocatalysis
  • Radical-polar crossover
  • Trifluoromethylacylation

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