Copper-Catalyzed Reaction of <i>N</i>-Monosubstituted Hydrazones with CBr<sub>4</sub>: Unexpected Fragmentation and Mechanistic Study

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Nenajdenko V. G., Kazakova A. A., Novikov A. S., Shikhaliyev N. G., Maharramov A. M., Qajar A. M., ...More

CATALYSTS, vol.13, no.8, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 13 Issue: 8
  • Publication Date: 2023
  • Doi Number: 10.3390/catal13081194
  • Journal Name: CATALYSTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, INSPEC, Metadex, Directory of Open Access Journals, Civil Engineering Abstracts
  • Azerbaijan State University of Economics (UNEC) Affiliated: Yes

Abstract

The copper catalyzed reaction of N-monosubstituted hydrazones with carbon tetrabromide leads to formation of expected dibromodiazadienes and unexpected dibromostyrenes. The experimental and theoretical study of the reaction revealed a key role of N-centered radicals, which can eliminate aryl radicals to form the corresponding dibromostyrenes. Alternatively, the oxidation of intermediate N-centered radicals by Cu(II) results in the corresponding diazadienes. These two reaction pathways are competitive directions of the reaction. Consequently, the reaction can be useful for the synthesis of both dibromostyrenes and rare dibromodiazadienes.