Login / Signup

Photoredox Catalysis: 1,4-Conjugate Addition of N-Methyl Radicals to Electron-Deficient Olefins via Decarboxylation of N-Substituted Acetic Acids.

Lakshmaiah GingipalliJeffrey BoerthDavid EmmonsTyler GrebeHolia Hatoum-MokdadBo PengLi ShaSharon TentarelliHaixia WangYe WuXiaoLan ZhengScott EdmondsonAriamala Gopalsamy
Published in: Organic letters (2020)
In this report, we describe a new photoredox catalyzed 1,4-conjugate addition of N-substituted acetic acids to electron-deficient olefins via decarboxylative C-C bond formation. This C-C bond formation occurred under mild conditions enabled by visible light irradiation. This transformation facilitated the synthesis of biologically relevant N-substituted heterocyclic structural motifs not readily accessible by other methods. The C-C bond formation protocol was applied to weakly nucleophilic heterocycles such as indoles, indazoles, imidazoles, and cyclic amides to form functionalized drug-like small molecule.
Keyphrases
  • visible light
  • small molecule
  • molecular docking
  • randomized controlled trial
  • electron transfer
  • cancer therapy
  • transition metal
  • adverse drug