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

An efficient, metal‐free oxidation method of the N‐ortho C(sp3)−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...

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Veröffentlicht in:Asian journal of organic chemistry 2022-12, Vol.11 (12), p.n/a
Hauptverfasser: Chang, Huan‐Huan, He, Xing‐Xian, Zang, Zhong‐Lin, Zhou, Cheng‐He, Cai, Gui‐Xin
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Sprache:eng
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Zusammenfassung:An efficient, metal‐free oxidation method of the N‐ortho C(sp3)−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 H2O offered the main oxygen source to achieve greener photochemical C(sp3)−H oxidation. A metal‐free oxidation of the N‐ortho C(sp3)−H bond of amides to imides via visible‐light‐assisted homolytic cleavage of the N−Br bond of NBS has been developed. H2O offered the main oxygen source to achieve greener photochemical C(sp3)−H oxidation.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200500