Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

Scholarly Works

• Gupta, G.; Ray, K.; Singh, P.; Mothsra, P.; Efimov, I.; Elizaveta, Y.; Jain, A.; Ravi, R.; Mishra, A.; Aggarwal, A. K.; Singh, A. K.; Kumar, Y. CH Functionalization and Cyclization Reactions Using Hypervalent Iodine Reagents: A Review on Synthetic Applications. European Journal of Organic Chemistry 2025. doi:10.1002/ejoc.202500110
• Lopat'eva, E. R.; Krylov, I. B.; Yu, B.; Terent'ev, A. O. N‐Oxyl Radicals in Oxidative C−O Coupling: Free‐Radical Hydrogen Substitution and Addition to C=C Bonds. Asian Journal of Organic Chemistry 2024, 14. doi:10.1002/ajoc.202400503
• Reetu, R.; Gujjarappa, R.; Teli, Y. A.; Patel, M. J.; Kalita, S.; Dash, S.; Ghanta, S.; Keremane, K. S.; Singh, V.; El‐marghany, A.; Malakar, C. C. Transformation of Unactivated Alkenes into Iodohydrins and β‐Iodoethers using Iodine‐DMSO as a Reagent Combination. ChemistrySelect 2024, 9. doi:10.1002/slct.202304426
• Sakkani, N.; Jha, D. K.; Sadiq, N.; Sharif, P.; Zhao, J. C. Synthesis of phenyliodine(III) bis(3-bromopropionate) for an organocatalyzed Markovnikov-type bromo-aminoxidation of vinylarenes. Green Synthesis and Catalysis 2023, 4, 316–320. doi:10.1016/j.gresc.2023.06.001
• Leifert, D.; Studer, A. Organic Synthesis Using Nitroxides. Chemical reviews 2023, 123, 10302–10380. doi:10.1021/acs.chemrev.3c00212
• Liu, J.; Jin, J.; Zhang, K.; Cai, L. Alkoxy Radical Induced Transformations from N‐Alkoxyphthalimides Under the Photoredox Catalysis. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202300160
• Vittal, S.; Mujahid Alam, M.; Hussien, M.; Amanullah, M.; Pisal, P. M.; Ravi, V. Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update. ChemistrySelect 2023, 8. doi:10.1002/slct.202204240
• Sihag, M.; Soni, R.; Rani, N.; Kinger, M.; Kumar Aneja, D. Recent Synthetic Applications of Hypervalent Iodine Reagents. A Review in Three Installments: Installment II. Organic Preparations and Procedures International 2022, 55, 99–159. doi:10.1080/00304948.2022.2114236
• Luan, S.; Castanheiro, T.; Poisson, T. Electrochemical Synthesis of Iodohydrins. Advanced Synthesis & Catalysis 2022, 364, 2741–2747. doi:10.1002/adsc.202200470
• Budnikov, A. S.; Krylov, I. B.; Lastovko, A. V.; Yu, B.; Terent'ev, A. O. N‐Alkoxyphtalimides as Versatile Alkoxy Radical Precursors in Modern Organic Synthesis. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202200262
• Paveliev, S. A.; Segida, O. O.; Fedorova, U. V.; Mulina, O. M.; Terent'ev, A. O. Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene. Mendeleev Communications 2022, 32, 167–169. doi:10.1016/j.mencom.2022.03.004
• Tretyakov, E. V.; Ovcharenko, V. I.; Terent'ev, A. O.; Krylov, I. B.; Magdesieva, T. V.; Mazhukin, D. G.; Gritsan, N. P. Conjugated nitroxide radicals. Russian Chemical Reviews 2022, 91, RCR5025. doi:10.1070/rcr5025
• Krylov, I. B.; Paveliev, S. A.; Budnikov, A. S.; Segida, O. O.; Merkulova, V. M.; Vil, V. A.; Nikishin, G. I.; Terent'ev, A. O. Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds. Synthesis 2021, 54, 506–516. doi:10.1055/a-1643-7642
• Krylov, I. B.; Budnikov, A. S.; Lopat’eva, E. R.; Segida, O. O.; Paveliev, S. A.; Terent'ev, A. O. Electron-deficient N-oxyl radicals – new reagents for selective oxidative functionalization of organic substrates. Journal of Physics: Conference Series 2021, 1942, 012007. doi:10.1088/1742-6596/1942/1/012007
• Chen, R.; Liu, B.; Li, W.; Wang, K.-K.; Miao, C.; Li, Z.; Lv, Y.-J.; Liu, L. Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction. RSC advances 2021, 11, 8051–8054. doi:10.1039/d1ra00375e
• Paveliev, S. A.; Alimkhanova, L. S.; Sergeeva, A.; Terent'ev, A. O. Cerium(IV) ammonium nitrate promoted synthesis of O-phthalimide oximes from vinyl azides and N-hydroxyphthalimide. Tetrahedron Letters 2020, 61, 152533. doi:10.1016/j.tetlet.2020.152533
• Paveliev, S. A.; Churakov, A. I.; Alimkhanova, L. S.; Segida, O. O.; Nikishin, G. I.; Terent'ev, A. O. Electrochemical Synthesis of O‐Phthalimide Oximes from α‐Azido Styrenes via Radical Sequence: Generation, Addition and Recombination of Imide‐N‐Oxyl and Iminyl Radicals with C−O/N−O Bonds Formation. Advanced Synthesis & Catalysis 2020, 362, 3864–3871. doi:10.1002/adsc.202000618
• Chen, J. Y.; Selvaraju, M.; Lin, Y. T.; Dhole, S.; Lin, C. Y.; Sun, C.-M. Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles. The Journal of organic chemistry 2020, 85, 5570–5579. doi:10.1021/acs.joc.0c00421
• Wang, J.; Yi, W.-J. Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines. Molecules (Basel, Switzerland) 2019, 24, 3771. doi:10.3390/molecules24203771
• Krylov, I. B.; Paveliev, S. A.; Matveeva, O. K.; Terent'ev, A. O. Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide. Tetrahedron 2019, 75, 2529–2537. doi:10.1016/j.tet.2019.03.030

Explore citations to this article at