Practical photocatalytic trifluoromethylation and hydrotrifluoromethylation of styrenes in batch and flow

Natan J.W. Straathof, Sten E. Cramer, Volker Hessel, Timothy Noël

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110 Citations (Scopus)
185 Downloads (Pure)

Abstract

Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.

Original languageEnglish
Pages (from-to)15549-15553
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number50
DOIs
Publication statusPublished - 1 Jan 2016

Keywords

  • continuous flow
  • hydrotrifluoromethylation
  • microreactor
  • photoredox catalysis
  • trifluoromethylation

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