Visible‐light‐driven α‐Oxidation of Amide C(sp<sup>3</sup>)−H Bonds to Imides via <i>N</i>‐Bromosuccinimide and Water
Huan‐Huan Chang, Xing‐Xian He, Zhong‐Lin Zang, Cheng‐He Zhou, Gui‐Xin Cai
Abstract
Abstract An efficient, metal‐free oxidation method of the N ‐ ortho C(sp 3 )−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 showcased 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 )−H oxidation.
Topics & Concepts
ChemistryN-BromosuccinimideAmideVisible spectrumPhotochemistryHydrogen bondHydrogen atomMedicinal chemistryMoleculeOrganic chemistryHalogenationOptoelectronicsAlkylPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques