Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts

Victor D. Filimonov, Elena A. Krasnokutskaya, Assia Zh Kassanova, Valentina A. Fedorova, Ksenia S. Stankevich, Nikolay G. Naumov, Alexander A. Bondarev, Veronika A. Kataeva

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

Original languageEnglish
Pages (from-to)665-674
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number4
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • Aromatic substitution
  • Diazo compounds
  • Diazonium salts
  • Solvent effects
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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