Copper-catalyzed trifluoromethylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols

  • Xiaowu Liu
  • , Fei Xiong
  • , Xuanping Huang
  • , Liang Xu
  • , Pengfei Li
  • , Xiaoxing Wu

Research output: Contribution to journalArticlepeer-review

299 Scopus citations

Abstract

Not only symmetrical, but also unsymmetrical α,α-diaryl allylic alcohols are employed as substrates in the title reaction. A number of arenes and even heteroarenes underwent radical 1,2-aryl migration ("neophyl rearrangement") to produce α-aryl β-trifluoromethyl ketones. The preferential migration of electron-deficient aryl groups over electron-rich ones in unsymmetrical substrates supports the radical mechanism, which was further confirmed by DFT calculations.

Original languageEnglish
Pages (from-to)6962-6966
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number27
DOIs
StatePublished - 1 Jul 2013

Keywords

  • copper
  • migration
  • radical reactions
  • rearrangement
  • trifluoromethylation

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