Rapid trifluoromethylation and perfluoroalkylation of five-membered heterocycles by photoredox catalysis in continuous flow.
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).
Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven (The Netherlands).
Natan J W
NJ
Straathof
Hannes P L
HP
Gemoets
Xiao
X
Wang
Jaap C
JC
Schouten
Volker
V
Hessel
Timothy
T
Noël
D000478:Alkylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008027:Light; D009942:Organometallic Compounds / Q000737:chemistry; D055668:Photochemical Processes
D006571:Heterocyclic Compounds; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; C415768:tris(2,2'-bipyridyl)ruthenium(II)
flow chemistry; heterocycles; homogeneous catalysis; photochemistry; ruthenium