4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

J Am Chem Soc. 2021 Jan 20;143(2):964-972. doi: 10.1021/jacs.0c11138. Epub 2020 Dec 29.

Abstract

2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu as catalyst, we developed a visible-light-induced proton-coupled electron transfer strategy for the generation of phosphorus-centered radicals, via which a wide range of phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Electron Transport
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrocarbons, Aromatic / chemical synthesis*
  • Hydrocarbons, Aromatic / chemistry
  • Molecular Structure
  • Phosphorylation
  • Protons*

Substances

  • Heterocyclic Compounds
  • Hydrocarbons, Aromatic
  • Protons