title: Visible-light-promoted iminyl-radical formation from acyl oximes: a unified approach to pyridines, quinolines, and phenanthridines.
abstract: A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3 ] as a photoredox catalyst, the acyl oximes were converted by 1 e(-) reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.
authors: State Key Laboratory of Analytical Chemistry for Life Science and Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (China) http://hysz.nju.edu.cn/yanzhang/ http://hysz.nju.edu.cn/yusy/
authors: Heng
authors: H
authors: Jiang
authors: Xiaode
authors: X
authors: An
authors: Kun
authors: K
authors: Tong
authors: Tianyi
authors: T
authors: Zheng
authors: Yan
authors: Y
authors: Zhang
authors: Shouyun
authors: S
authors: Yu
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D002384:Catalysis; D005609:Free Radicals / Q000737:chemistry / Q000528:radiation effects; D007097:Imines / Q000737:chemistry* / Q000528:radiation effects; D008027:Light; D010091:Oximes / Q000737:chemistry* / Q000528:radiation effects; D010617:Phenanthridines / Q000138:chemical synthesis*; D055668:Photochemical Processes; D011725:Pyridines / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D000470:Alkaloids; D005609:Free Radicals; D007097:Imines; D010091:Oximes; D010617:Phenanthridines; D011725:Pyridines; D011804:Quinolines
keywords: N heteroarenes; acyl oximes; iminyl radicals; photochemistry; visible light