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A Mechanistic Investigation of the Visible‐Light Photocatalytic Trifluoromethylation of Heterocycles Using CF 3 I in Flow
Author(s) -
Su Yuanhai,
Kuijpers Koen P. L.,
König Niels,
Shang Minjing,
Hessel Volker,
Noël Timothy
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602596
Subject(s) - trifluoromethylation , photocatalysis , photochemistry , microreactor , quantum yield , chemistry , quenching (fluorescence) , yield (engineering) , trifluoromethyl , visible spectrum , combinatorial chemistry , computational chemistry , materials science , catalysis , organic chemistry , optoelectronics , physics , fluorescence , optics , alkyl , metallurgy
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 CF 3 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 CF 3 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.