Synthesis of azobenzenes with high reactivity towards reductive cleavage: Enhancing the repertoire of hypersensitive azobenzenes and examining their dissociation behavior

Taejun Eom, Anzar Khan

Research output: Contribution to journalArticle

Abstract

Trifluoromethyl (CF3), cyano (CN), and nitro (NO2) groups were demonstrated to be effective acceptors in the molecular design of triple-donor/acceptor-based hypersensitive azobenzenes. The synthesis of these reactive scaffolds requires only two steps with overall yields ranging from 70 to 73%. UV–Vis absorption spectroscopy indicated that in all cases, a few seconds of exposure to mild reducing conditions is sufficient for complete cleavage of the azo bond. Liquid chromatography coupled with mass spectrometry (LC-MS) established the formation of two aniline fragments in the case of the CF3 and CN-substituted azobenzenes. In the case of the NO2-substituted compound, however, partial reduction of the nitro group results in the formation of three different anilines.

Original languageEnglish
Article number152018
JournalTetrahedron Letters
Volume61
Issue number25
DOIs
Publication statusPublished - 2020 Jun 18

Keywords

  • Azo scission
  • Azobenzene reduction
  • Redox active
  • Reductive cleavage

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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