A mechanistic investigation of the visible light photocatalytic trifluoromethylation of heterocycles using CF3I in flow

Article

Su, Y., Kuijpers, K.P.L., Koenig, N., Shang, M., Hessel, V. & Noël, T. (2016). A mechanistic investigation of the visible light photocatalytic trifluoromethylation of heterocycles using CF3I in flow. Chemistry - A European Journal, 22(35), 12295-12300. In Scopus Cited 4 times.

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Abstract

 

Photocatalytic radical trifluoromethylation strategies have impacted the synthesis of trifluoromethyl-containing molecules. However, mechanistic aspects concerning such transformations remain poorly understood. Here, we describe in detail the mechanism of the visible-light photocatalytic trifluoromethylation of N-methylpyrrole with gaseous CF3I in flow. The use of continuous-flow microreactor technology allowed for the determination of different important parameters with high precision (e.g., photon flux, quantum yield, reaction rate constants) and for the handling of CF3I in a convenient manner. Our data indicates that the reaction occurs through a reductive quenching mechanism and that there is no radical chain process present.