Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts

Kenta Tanaka, Yuta Tanaka, Mami Kishimoto, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

An efficient synthesis of methoxy-substituted thioxanthylium salts has been developed. The reaction of diaryl sulfides with benzoyl chlorides in the presence of TfOH smoothly proceeded to give the desired thioxanthylium salts in good yields. In their UV–vis spectra, the maximum absorption wavelengths of methoxy-functionalized thioxanthylium salts were observed at around 460 nm, which show a drastic red shift compared to the parent thioxanthylium salts. The present reaction provides a versatile access to functionalized thioxanthylium salts, and therefore it constitutes a promising tool for the synthesis of biologically and photochemically active molecules.

Original languageEnglish
Pages (from-to)2105-2112
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - Sep 5 2019
Externally publishedYes

Keywords

  • Friedel–Crafts reaction
  • Metal-free conditions
  • One-pot synthesis
  • Photoredox catalyst
  • Thioxanthylium salt

ASJC Scopus subject areas

  • Organic Chemistry

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