Premium
Rapid Trifluoromethylation and Perfluoroalkylation of Five‐Membered Heterocycles by Photoredox Catalysis in Continuous Flow
Author(s) -
Straathof Natan J. W.,
Gemoets Hannes P. L.,
Wang Xiao,
Schouten Jaap C.,
Hessel Volker,
Noël Timothy
Publication year - 2014
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201301282
Subject(s) - trifluoromethylation , photoredox catalysis , chemistry , flow chemistry , photocatalysis , continuous flow , combinatorial chemistry , catalysis , organic chemistry , microreactor , trifluoromethyl , nanotechnology , biochemical engineering , materials science , alkyl , engineering
Abstract Trifluoromethylated and perfluoroalkylated heterocycles are important building blocks for the synthesis of numerous pharmaceutical products, agrochemicals and are widely applied in material sciences. To date, trifluoromethylated and perfluoroalkylated hetero‐aromatic systems can be prepared utilizing visible light photoredox catalysis methodologies in batch. While several limitations are associated with these batch protocols, the application of microflow technology could greatly enhance and intensify these reactions. A simple and straightforward photocatalytic trifluoromethylation and perfluoroalkylation method has been developed in continuous microflow, using commercially available photocatalysts and microflow components. A selection of five‐membered hetero‐aromatics were successfully trifluoromethylated (12 examples) and perfluoroalkylated (5 examples) within several minutes (8–20 min).