One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid

Scholarly Works

• Dohi, T.; Elboray, E. E.; Kikushima, K.; Morimoto, K.; Kita, Y. Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations. Chemical reviews 2025, 125, 3440–3550. doi:10.1021/acs.chemrev.4c00808
• Bennett, C. W.; McDonald, N. R.; Siddiqui, A.; Romero, E. A. Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts. ChemPhotoChem 2024, 9. doi:10.1002/cptc.202400285
• Yoshimura, A.; Zhdankin, V. V. Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents. Chemical reviews 2024, 124, 11108–11186. doi:10.1021/acs.chemrev.4c00303
• Avramidou, E.; Triandafyllou, A. K.; Zisopoulou, S. A.; Stini, N. A.; Demertzidou, V. P.; Kokotos, C. G.; Gkizis, P. L.; Gallos, J. K. Iodonium Salt‐Mediated Oxidation of Sulfides to Sulfoxides by DMSO. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202400596
• Soldatova, N. S.; Radzhabov, A. D.; Ivanov, D. M.; Burguera, S.; Frontera, A.; Abramov, P. A.; Postnikov, P. S.; Kukushkin, V. Y. Key-to-lock halogen bond-based tetragonal pyramidal association of iodonium cations with the lacune rims of beta-octamolybdate. Chemical science 2024, 15, 12459–12472. doi:10.1039/d4sc01695e
• Galicia, J.; McDonald, N. R.; Bennett, C. W.; He, J.; Glossbrenner, M. D.; Romero, E. A. Exogenous photocatalyst-free aryl radical generation from diaryliodonium salts and use in metal-catalyzed C-H arylation. Chemical communications (Cambridge, England) 2024, 60, 6929–6932. doi:10.1039/d4cc01259c
• Yuan, H.; Yin, W.; Hu, J.; Li, Y. 3-sulfonyloxyaryl(mesityl)iodonium triflates as 1,2-benzdiyne precursors with activation via ortho-deprotonative elimination strategy. Nature communications 2023, 14, 1841. doi:10.1038/s41467-023-37196-3
• Knieb, A.; Krishnamurti, V.; Zhu, Z.; K Surya Prakash, G. Synthesis of Monofluoromethylarenes: Direct Monofluoromethylation of Diaryliodonium Bromides using Fluorobis(phenylsulfonyl)methane (FBSM). Journal of Fluorine Chemistry 2023, 267, 110095. doi:10.1016/j.jfluchem.2023.110095
• Soldatova, N. S.; Suslonov, V. V.; Ivanov, D. M.; Yusubov, M. S.; Resnati, G.; Postnikov, P. S.; Kukushkin, V. Y. Controlled Halogen-Bond-Involving Assembly of Double-σ-Hole-Donating Diaryliodonium Cations and Ditopic Arene Sulfonates. Crystal Growth & Design 2022, 23, 413–423. doi:10.1021/acs.cgd.2c01090
• Pham, W. Principles for the Design of PET Probes. Principles of Molecular Probe Design and Applications; Springer Nature Singapore, 2022; pp 79–145. doi:10.1007/978-981-19-5739-0_3
• Aliyarova, I. S.; Tupikina, E. Y.; Soldatova, N. S.; Ivanov, D. M.; Postnikov, P. S.; Yusubov, M.; Kukushkin, V. Y. Halogen Bonding Involving Gold Nucleophiles in Different Oxidation States. Inorganic chemistry 2022, 61, 15398–15407. doi:10.1021/acs.inorgchem.2c01858
• Alvi, S.; Jayant, V.; Ali, R. Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era. ChemistrySelect 2022, 7. doi:10.1002/slct.202200704
• Soldatova, N. S.; Postnikov, P. S.; Ivanov, D. M.; Semyonov, O. V.; Kukurina, O. S.; Guselnikova, O.; Yamauchi, Y.; Wirth, T.; Zhdankin, V. V.; Yusubov, M. S.; Gomila, R. M.; Frontera, A.; Resnati, G.; Kukushkin, V. Y. Zwitterionic iodonium species afford halogen bond-based porous organic frameworks. Chemical science 2022, 13, 5650–5658. doi:10.1039/d2sc00892k
• Chen, Y.; Gu, Y.; Meng, H.; Shao, Q.; Xu, Z.; Bao, W.; Gu, Y.; Xue, X.; Zhao, Y. Metal‐Free C−H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand. Angewandte Chemie 2022, 134. doi:10.1002/ange.202201240
• Chen, Y.; Gu, Y.; Meng, H.; Shao, Q.; Xu, Z.; Bao, W.; Gu, Y.; Xue, X.-S.; Zhao, Y. Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand. Angewandte Chemie (International ed. in English) 2022, 61, e202201240. doi:10.1002/anie.202201240
• Kikushima, K.; Elboray, E. E.; Jiménez-Halla, J. O. C.; Solorio-Alvarado, C. R.; Dohi, T. Diaryliodonium(III) salts in one-pot double functionalization of C-IIII and ortho C-H bonds. Organic & biomolecular chemistry 2022, 20, 3231–3248. doi:10.1039/d1ob02501e
• Rossi, R.; Ciofalo, M. Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art. Current Organic Chemistry 2022, 26, 215–274. doi:10.2174/1385272826666220201124008
• Soldatova, N. S.; Semenov, A. V.; Geyl, K. K.; Baykov, S. V.; Shetnev, A.; Konstantinova, A. S.; Korsakov, M. M.; Yusubov, M. S.; Postnikov, P. S. Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts. Advanced Synthesis & Catalysis 2021, 363, 3566–3576. doi:10.1002/adsc.202100426
• Elsherbini, M.; Moran, W. J. Scalable electrochemical synthesis of diaryliodonium salts. Organic & biomolecular chemistry 2021, 19, 4706–4711. doi:10.1039/d1ob00457c
• Antonkin, N. S.; Vlasenko, Y. A.; Yoshimura, A.; Smirnov, V. I.; Borodina, T. N.; Zhdankin, V. V.; Yusubov, M. S.; Shafir, A.; Postnikov, P. S. Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts. The Journal of organic chemistry 2021, 86, 7163–7178. doi:10.1021/acs.joc.1c00483

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