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Journal of Flow Chemistry

, Volume 9, Issue 1, pp 9–12 | Cite as

Continuous flow palladium-catalyzed trifluoromethylthiolation of C-H bonds

  • Alexanne Bouchard
  • Vanessa Kairouz
  • Maxime Manneveau
  • Heng-Ying Xiong
  • Tatiana BessetEmail author
  • Xavier Pannecoucke
  • Hélène LebelEmail author
Communications

Abstract

A continuous flow process for the synthesis of trifluoromethylthioethers is reported. The palladium-catalyzed C-H trifluoromethylthiolation of amides derived from the 8-aminoquinoline using N-[(trifluoromethyl)thio]phthalimide produced the desired products in moderate to good yields with a residence time of 20 min. In comparison with the batch process, the reaction time was decreased by a factor of 100 to 200, demonstrating the positive effect of continuous flow processes for this type of reaction.

Keywords

Aminoquinoline Bidentate directing group C-SCF3 bond Organofluorine compounds Flow process C-H activation Halogenation Trifluoromethylthioethers 

Notes

Acknowledgments

This research was supported by the Natural Science and Engineering Research Council of Canada (NSERC) under the CREATE Training Program in Continuous Flow Science, a discovery grant from NSERC (Canada), the Canada Foundation for Innovation, the Université de Montréal and the Centre in Green Chemistry and Catalysis (CGCC). We would like to thank Alexandra Furtos from the Regional Mass Spectrometry Centre and Sylvie Bilodeau from the Regional Centre of NMR spectroscopy of the Université de Montréal. H.-Y.X. thanks CSC for fellowship.

Supplementary material

41981_2018_23_MOESM1_ESM.pdf (2.1 mb)
(PDF 2.13 mb)

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Copyright information

© Akadémiai Kiadó 2018

Authors and Affiliations

  1. 1.Department of Chemistry and Continuous Flow Synthesis LaboratoryUniversité de MontréalMontréalCanada
  2. 2.INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014)Normandie UniversitéRouenFrance

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