Metal‐Free Direct CH Perfluoroalkylation of Arenes and Heteroarenes Using a Photoredox Organocatalyst

Abstract

We report the visible‐light‐induced trifluoromethylation of arenes and heteroarenes using sodium trifluoromethanesulfinate catalyzed by anthraquinone‐2‐carboxylic acid. This reaction is a metal‐free trifluoromethylation of arenes and heteroarenes catalyzed by a photoredox organocatalyst. Perfluoroalkylated arenes were also produced using sodium perfluoroalkylsulfinates.magnified image

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

“…The group utilised the corresponding fluoroalkyl sulfinate salt as the fluoroalkyl source, in combination with TFA and Acid Red 94 as the photocatalyst, under 22 W fluorescent lamp irradiation to perform the transformation (Scheme 28) [72]. …”

Photocatalytic fluoroalkylation reactions of organic compounds

“…94,95 Excellent review articles do exist on photoorganocatalysis. 9 Once the optimized reaction conditions for trifluoromethylation are met, 106 the scope and limitations of the reaction can be explored in Scheme 41. Electron-rich arenes afford the corresponding products in good yields.…”

Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides

“…[19][20][21][22] Fukuzumi reported the photoredox catalytic conversion of benzene to phenol with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under visible-light irradiation. [23] Itoh and subsequently Yuan reported the trifluoromethylations of arenes and heteroarenes with anthraquinone-2-carboxylic acid [24] and abstraction or C-C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion.…”