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

Org Lett. 2020 May 1;22(9):3418-3422. doi: 10.1021/acs.orglett.0c00873. Epub 2020 Apr 20.

Abstract

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.

MeSH terms

  • Acetates / chemistry
  • Alkenes* / chemistry
  • Catalysis
  • Decarboxylation
  • Electrons*
  • Methane / analogs & derivatives

Substances

  • Acetates
  • Alkenes
  • methyl radical
  • Methane