Electrolyte‐Triggered C5‐Selective Trifluoromethylation and Halogenation of 8‐Aminoquinoline Derivatives

Abstract

An efficient electrolyte‐triggered trifluoromethylation and halogenation at C5 position of 8‐aminoquinoline derivatives was developed, affording the C−H functionalization products in moderate to excellent yields. Furthermore, the mild and green reactions had lower energy consumption and shorter times. Most importantly, both transition‐metal catalysts and oxidants were avoided.

Photo/electrocatalytic site-selective C–H functionalization of 8-aminoquinolines and their analogues

“…To the best of our knowledge, this is the only report on the electrocatalytic C3-H functionalization of 8-aminoquinolines. Although the reaction conditions of this method were similar to those reported by Xie et al, 60 the reaction products were completely different ( product 249 was characterized using nuclear magnetic resonance). The only limitation of this work is that the explicit structure of product 249 has not been demonstrated.…”

“…32a). 60 The reaction requires neither a transition metal catalyst nor an external chemical oxidant and uses graphite and a platinum plate as the anode and cathode, respectively, as well as n Bu 4 NBF 4 as the electrolyte, and acetonitrile as the solvent at a constant current of 15 mA. This reaction has a wide range of substrate applications.…”

Harnessing photocatalytic and electrochemical approaches for C–H bond trifluoromethylation and fluoroalkylation

“…To deal with this, Chen et al Recently, Xie and team extended the electrochemical C-H trifluoromethylation to 8-aminoquinoline derivatives 121 regioselectively at the C-5 position 125 using Langlois reagent 66 in an undivided cell setup (Scheme 114). 195 Chiang et al improved upon their previous photoredox approach 64 for biocompatible trifluoromethylation of tryptophan peptide 68 by replicating their previous reaction conditions employing an electrochemical method (Scheme 115). 196 This method is much more effective compared with the previous approach, as it utilises ferrocene in place of the expensive Ir-based catalyst.…”

“…Recently, Xie and team extended the electrochemical C–H trifluoromethylation to 8-aminoquinoline derivatives 121 regioselectively at the C-5 position 125 using Langlois reagent 66 in an undivided cell setup (Scheme 114). 195…”