Oxime radicals: generation, properties and application in organic synthesis

Igor B. Krylov, Stanislav A. Paveliev, Alexander S. Budnikov and Alexander O. Terent’ev
Beilstein J. Org. Chem. 2020, 16, 1234–1276. https://doi.org/10.3762/bjoc.16.107

Cite the Following Article

Oxime radicals: generation, properties and application in organic synthesis
Igor B. Krylov, Stanislav A. Paveliev, Alexander S. Budnikov and Alexander O. Terent’ev
Beilstein J. Org. Chem. 2020, 16, 1234–1276. https://doi.org/10.3762/bjoc.16.107

How to Cite

Krylov, I. B.; Paveliev, S. A.; Budnikov, A. S.; Terent’ev, A. O. Beilstein J. Org. Chem. 2020, 16, 1234–1276. doi:10.3762/bjoc.16.107

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 185.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Parsons, A. F.; Parsons, T. F. doi:10.1002/9781119716846.ch13
  • Moloney, M. G. doi:10.1002/9781119716846.ch1
  • Banerji, K. K. doi:10.1002/9781119716846.ch3
  • Chen, W.; Wu, Y.; Jiang, Y.; Yang, G.; Li, Y.; Xu, L.; Yang, M.; Wu, B.; Pan, Y.; Xu, Y.; Liu, Q.; Chen, C.; Peng, F.; Wang, S.; Zou, Y. Catalyst Selection over an Electrochemical Reductive Coupling Reaction toward Direct Electrosynthesis of Oxime from NOx and Aldehyde. Journal of the American Chemical Society 2024, 146, 6294–6306. doi:10.1021/jacs.3c14687
  • Tretyakov, E. Preparation and characterization of magnetic and magnetophotonic materials based on organic free radicals. Organic Radicals; Elsevier, 2024; pp 61–181. doi:10.1016/b978-0-443-13346-6.00005-1
  • Zayakin, I.; Romanenko, G.; Bagryanskaya, I.; Ugrak, B.; Fedin, M.; Tretyakov, E. Catalytic System for Cross-Coupling of Heteroaryl Iodides with a Nitronyl Nitroxide Gold Derivative at Room Temperature. Molecules (Basel, Switzerland) 2023, 28, 7661. doi:10.3390/molecules28227661
  • Park, J.; Kim, J.; Jeong, G. Y.; Kim, Y.; Lee, E. Uncovering Nitrosyl Reactivity at N‐Heterocyclic Carbene Center. Angewandte Chemie 2023, 135. doi:10.1002/ange.202314978
  • Park, J.; Kim, J.; Jeong, G. Y.; Kim, Y.; Lee, E. Uncovering Nitrosyl Reactivity at N-Heterocyclic Carbene Center. Angewandte Chemie (International ed. in English) 2023, 62, e202314978. doi:10.1002/anie.202314978
  • Budnikov, A. S.; Krylov, I. B.; Lastovko, A. V.; Dolotov, R. A.; Shevchenko, M. I.; Terent'ev, A. O. The diacetyliminoxyl radical in oxidative functionalization of alkenes. Organic & biomolecular chemistry 2023, 21, 7758–7766. doi:10.1039/d3ob00925d
  • Lazarević, J.; Ilić, K.; Zvezdanović, J.; Stojanović, G. Synthesis, characterization and evaluation of the simple benzaldoximes protective effect against lipid peroxidation. Chemical Papers 2023, 78, 331–341. doi:10.1007/s11696-023-03090-x
  • Lopat'eva, E. R.; Krylov, I. B.; Paveliev, S. A.; Emtsov, D. A.; Kostyagina, V. A.; Korlyukov, A. A.; Terent'ev, A. O. Free Radicals in the Queue: Selective Successive Addition of Azide and N-Oxyl Radicals to Alkenes. The Journal of organic chemistry 2023, 88, 13225–13235. doi:10.1021/acs.joc.3c01470
  • Leifert, D.; Studer, A. Organic Synthesis Using Nitroxides. Chemical reviews 2023, 123, 10302–10380. doi:10.1021/acs.chemrev.3c00212
  • Wang, P.-Z.; Chen, J.-R.; Xiao, W.-J. Emerging Trends in Copper-Promoted Radical-Involved C-O Bond Formations. Journal of the American Chemical Society 2023, 145, 17527–17550. doi:10.1021/jacs.3c04879
  • Zhang, S.; De Leon Rodriguez, L. M.; Li, F. F.; Brimble, M. A. Recent developments in the cleavage, functionalization, and conjugation of proteins and peptides at tyrosine residues. Chemical science 2023, 14, 7782–7817. doi:10.1039/d3sc02543h
  • Budnikov, A. S.; Krylov, I. B.; Ushakov, I. E.; Subbotina, I. R.; Monin, F. K.; Nikishin, G. I.; Efimov, N. N.; Gorbunov, D. E.; Gritsan, N. P.; Tretyakov, E. V.; Yu, B.; Terent'ev, A. O. Two Discoveries in One Crystal: σ-Type Oxime Radical as an Unforeseen Building Block in Molecular Magnetics and Its Spatial Structure. Inorganic chemistry 2023, 62, 10965–10972. doi:10.1021/acs.inorgchem.3c00947
  • Budnikov, A. S.; Krylov, I. B.; Mulina, O. M.; Lapshin, D. A.; Terent'ev, A. O. CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals. Advanced Synthesis & Catalysis 2023, 365, 1714–1755. doi:10.1002/adsc.202300144
  • Oisaki, K. 計画的偶発性マインドがもたらした研究キャリア. Journal of Synthetic Organic Chemistry, Japan 2023, 81, 366–380. doi:10.5059/yukigoseikyokaishi.81.366
  • Wei, M.; Liu, C.; Wang, C.-S.; Li, Y.; Qiu, P.; Dong, Q.; Yang, Z.; Fang, Z.; Guo, K. Synthesis of pyrido[1,2-a]indol-6(7H)-ones via a visible light-photocatalyzed formal (4 + 2) cycloaddition of indole-derived bromides and alkenes or alkynes. Green Chemistry 2023, 25, 2453–2457. doi:10.1039/d2gc04491a
  • Chen, J.; Lu, G.; Hao, Y.; Lu, Y.; Huang, L.; Zhang, Y. Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation. Advanced Materials Interfaces 2023, 10. doi:10.1002/admi.202201882
  • Budnikov, A. S.; Krylov, I. B.; Kuzmin, I. V.; Segida, O. O.; Lastovko, A. V.; Shevchenko, M. I.; Nikishin, G. I.; Terent'ev, A. O. Diacetyliminoxyl as a selective radical reagent for organic synthesis: dehydrogenation and dehydrogenative C–O coupling reactions. Organic Chemistry Frontiers 2023, 10, 388–398. doi:10.1039/d2qo01649d
Other Beilstein-Institut Open Science Activities