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RAS PresidiumДоклады Российской академии наук. Химия, науки о материалах Doklady Chemistry

  • ISSN (Print) 2686-9535
  • ISSN (Online) 3034-5111

Study of the mechanism of copper-activated NHC–R and NHC=O coupling under the conditions of the Chan–Evans–Lam reaction system

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PII
S3034511125010019-1
DOI
10.7868/S3034511125010019
Publication type
Article
Status
Published
Authors
A. S. Galushko
  • Affiliation: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Volume/ Edition
Volume 520 / Issue number 1
Pages
3-11
Abstract
In this work, the phenomena of copper-induced formation of NHC-R and NHC=O particles in the Chan–Evans–Lam arylation reaction system of aniline are discussed for the first time. The considered combinations between NHC and arylboronic acid residues have been demonstrated using 5 different arylboronic acids and three Cu/NHC complexes. It is also shown that the formation of the azolone NHC=O is due to copper-mediated oxygen transfer from the atmosphere to the carbene center of the NHC. Using a set of experimental physicochemical methods of analysis, as well as with the help and methods of quantum chemistry, it is shown for the first time that the degradation pathway of Cu/NHC complexes through the formation of NHC–R is controlled kinetically, and through the formation of NHC=O - thermodynamically, which makes a significant contribution to the understanding of the observed phenomena.
Keywords
кросс-сочетание медь NHC реакция Чана–Эванса–Лама масс-спектрометрия электронная микроскопия
Date of publication
18.09.2025
Year of publication
2025
Number of purchasers
0
Views
5

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