Continuous flow palladium-catalyzed trifluoromethylthiolation of C-H bonds

Alexanne Bouchard (1) , Vanessa Kairouz (1) , Maxime Manneveau (2) , Heng-Ying Xiong (2) , Tatiana Besset (2) , Xavier Pannecoucke (2) , Hélène Lebel (1)

1 UdeM - Université de Montréal
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Domains: Chemical Sciences

Alexanne Bouchard, Vanessa Kairouz, Maxime Manneveau, Heng-Ying Xiong, Tatiana Besset, et al.. Continuous flow palladium-catalyzed trifluoromethylthiolation of C-H bonds. Journal of flow chemistry, 2019, 9 (1), pp.9-12. ⟨10.1007/s41981-018-0023-4⟩. ⟨hal-02330475⟩