title: A Mechanistic Investigation of the Visible-Light Photocatalytic Trifluoromethylation of Heterocycles Using CF3 I in Flow.
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 CF3 I 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 CF3 I 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.
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.|Department of Chemical Engineering, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, P.R. China.
authors.forename: Yuanhai
authors.initials: Y
authors.lastname: Su
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Koen P L
authors.initials: KP
authors.lastname: Kuijpers
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Niels
authors.initials: N
authors.lastname: König
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Minjing
authors.initials: M
authors.lastname: Shang
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Volker
authors.initials: V
authors.lastname: Hessel
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands. t.noel@tue.nl.
authors.forename: Timothy
authors.initials: T
authors.lastname: Noël
keywords: continuous flow; microreactors; photocatalysis; trifluoromethylation; visible light