Visible‐light‐driven α‐Oxidation of Amide C(sp³)−H Bonds to Imides via N‐Bromosuccinimide and Water

Abstract

An efficient, metal-free oxidation method of the Northo C(sp 3 )À H bond of amide via visible-light irradiation has been developed. A broad range of imides can be facilely obtained at room temperature and this protocol is show-cased in the gram-scale synthesis. Preliminary mechanistic studies revealed that a hydrogen atom transfer (HAT) process was involved and H 2 O offered the main oxygen source to achieve greener photochemical C(sp 3 )À H oxidation.

Discovery of Trifluorobutene Amide Derivatives as Potential Nematicides: Design, Synthesis, Nematicidal Activity Evaluation, SAR, and Mode of Action Study

“…General Synthetic Procedure for Target Compounds. 39 To a 100 mL single-necked bottle, acid (4 mmol) and dichloromethane (15 mL) were added, and then oxalyl chloride (5 mmol) dissolved in dichloromethane (10 mL) was added dropwise into the reaction solution at 0 °C. After that, dimethylformamide (0.05 mL) was added, and the mixture was stirred at room temperature for 3 h. After reaction completion monitoring by TLC, the solvent was removed under reduced pressure to afford the corresponding acyl chloride, which was directly used in the next step.…”

Sustainable electrocatalytic oxidation of N-alkylamides to acyclic imides using H2O

“…In 2022, Cai and colleagues reported an efficient metal-free, photoinduced strategy for the α-oxidation of N -alkylamides through a hydrogen atom transfer (HAT) process. 27 However, this method required an excess of N -bromosuccinimide (NBS) as the HAT reagent. Hence, there remains a pressing need for more sustainable and efficient methods for the α-oxidation of N -alkylamides in imide synthesis that exhibit high atom-efficiency and chemoselectivity.…”