Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 35, Pages 12295-12300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602596
Keywords
continuous flow; microreactors; photocatalysis; trifluoromethylation; visible light
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Funding
- European Union [622415]
- VIDI grant [14150]
- Marie Curie CIG grant [333659]
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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.
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