Visible Light Promotes Cascade Trifluoromethylation/Cyclization, Leading to Trifluoromethylated Polycyclic Quinazolinones, Benzimidazoles and Indoles

Molecules. 2022 Dec 1;27(23):8389. doi: 10.3390/molecules27238389.

Abstract

Efficient visible-light-induced radical cascade trifluoromethylation/cyclization of inactivated alkenes with CF3Br, which is a nonhygroscopic, noncorrosive, cheap and industrially abundant chemical, was developed in this work, producing trifluoromethyl polycyclic quinazolinones, benzimidazoles and indoles under mild reaction conditions. The method features wide functional group compatibility and a broad substrate scope, offering a facile strategy to pharmaceutically produce valuable CF3-containing polycyclic aza-heterocycles.

Keywords: bromotrifluoromethane; cyclization; polycyclic benzimidazole; polycyclic indole; polycyclic quinazolinone; trifluoromethylation; visible-light induction.

MeSH terms

  • Benzimidazoles*
  • Catalysis
  • Indoles*
  • Light
  • Quinazolinones

Substances

  • Indoles
  • Benzimidazoles
  • Quinazolinones