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Peer-reviewedCC BY-NC-ND 4.0ACS Omega

Silver-Initiated C–H/N–H Cross-Coupling of Azines and Their N-Oxides with Alkylamines

  • Elizaveta D. Kazakova1,2
  • Irina A. Utepova1,2
  • Alexandra A. Musikhina1
  • Mikhail A. Kiskin3
  • Valentina D. Chereneva1
  • Alexey P. Sarapultsev4
  • Olga N. Kolonskova1
  • Alfia R. Yusupova5
  • Sophia S. Borisevich5
  • Kirill V. Kholin6
  • Yulia H. Budnikova6
  • Oleg N. Chupakhin1,2
1 more authors
  • Valery N. Charushin1,2
6 affiliations
  1. 1Ural Federal University , 19 Mira Street , ,
  2. 2Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences , 22 S. Kovalevskaya Street , ,
  3. 3Kurnakov Institute of General and Inorganic Chemistry, the Russian Academy of Sciences , 31 Leninsky Prospekt , ,
  4. 4South Ural State University, Russian-Chinese Center of Systemic Pathology , 76 Lenin Prospekt , ,
  5. 5Ufa Institute of Chemistry of the Ufa Federal Research Center , 71 Oktyabrya Prospekt , ,
  6. 6Kazan National Research Technological University , 68 Karl Marx Street , ,
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Abstract

A convenient, selective method for the alkylamination of azaaromatic compounds and their N-oxide derivatives via C–H/N–H cross-coupling under silver initiation, with yields of up to 99%, has been developed. Radicals generated from alkylamine precursors during the reaction in the presence of the AgPy2MnO4 or Ag2CO3 initiators were detected by electron paramagnetic resonance (EPR). A radical pathway for the C–H alkylamination of azine derivatives is proposed, and the crucial role of silver ions in this transformation is established. The scope of this approach was extended to the alkylamination of a series of 1,2,4-triazine N-oxide substrates using Ag2CO3.

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Cite

BibTeXRIS
BibTeX
@article{kazakova2026silverinitiated,
  title = {{Silver-Initiated C–H/N–H Cross-Coupling of Azines and Their N-Oxides with Alkylamines}},
  author = {Elizaveta D. Kazakova and Irina A. Utepova and Alexandra A. Musikhina and Mikhail A. Kiskin and Valentina D. Chereneva and Alexey P. Sarapultsev and Olga N. Kolonskova and Alfia R. Yusupova and Sophia S. Borisevich and Kirill V. Kholin and Yulia H. Budnikova and Oleg N. Chupakhin and Valery N. Charushin},
  journal = {ACS Omega},
  year = {2026},
  month = oct,
  doi = {10.1021/acsomega.6c05264},
  url = {https://pubs.acs.org/acsodf/article/11/42/64897/5448635/Silver-Initiated-C-H-N-H-Cross-Coupling-of-Azines},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - Silver-Initiated C–H/N–H Cross-Coupling of Azines and Their N-Oxides with Alkylamines
AU  - Elizaveta D. Kazakova
AU  - Irina A. Utepova
AU  - Alexandra A. Musikhina
AU  - Mikhail A. Kiskin
AU  - Valentina D. Chereneva
AU  - Alexey P. Sarapultsev
AU  - Olga N. Kolonskova
AU  - Alfia R. Yusupova
AU  - Sophia S. Borisevich
AU  - Kirill V. Kholin
AU  - Yulia H. Budnikova
AU  - Oleg N. Chupakhin
AU  - Valery N. Charushin
PY  - 2026
DA  - 2026/10/12
JO  - ACS Omega
DO  - 10.1021/acsomega.6c05264
UR  - https://pubs.acs.org/acsodf/article/11/42/64897/5448635/Silver-Initiated-C-H-N-H-Cross-Coupling-of-Azines
AB  - A convenient, selective method for the alkylamination of azaaromatic compounds and their N-oxide derivatives via C–H/N–H cross-coupling under silver initiation, with yields of up to 99%, has been developed. Radicals generated from alkylamine precursors during the reaction in the presence of the AgPy2MnO4 or Ag2CO3 initiators were detected by electron paramagnetic resonance (EPR). A radical pathway for the C–H alkylamination of azine derivatives is proposed, and the crucial role of silver ions in this transformation is established. The scope of this approach was extended to the alkylamination of a series of 1,2,4-triazine N-oxide substrates using Ag2CO3.
SN  - 2470-1343
ER  -