Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

Scholarly Works

• Zhang, J.; Su, R.; Liu, W. Radical di- and multi-functionalization of alkenes: recent advances in diverse reaction modes utilizing TBHP as reactants. Organic Chemistry Frontiers 2025, 12, 5683–5716. doi:10.1039/d5qo00785b
• Su, R.; Zhang, J.; Jiang, Y.; Jiang, X.; Zhou, P.; Jiang, J.; Liu, W. Visible light-driven regioselective tert-butyl peroxidation and hydroperoxidation of alkenes using TBHP. Green Chemistry 2025, 27, 9958–9967. doi:10.1039/d5gc02911b
• Bityukov, O. V.; Serdyuchenko, P. Y.; Kirillov, A. S.; Nikishin, G. I.; Vil', V. A.; Terent'ev, A. O. Advances in radical peroxidation with hydroperoxides. Beilstein journal of organic chemistry 2024, 20, 2959–3006. doi:10.3762/bjoc.20.249
• Varala, R.; Seema, V.; Hussein, M.; Alam, M. M.; Beda, D. P. tert ‐Butyl Hydroperoxide (TBHP): Recent Progress in C−H Functionalization and Heteroatom‐Heteroatom Bond Formations. ChemistrySelect 2024, 9. doi:10.1002/slct.202401937
• Tan, P.; Wang, S.; Li, G.; Wang, H.; Zhao, Z.; Jiang, H.; Xie, L.; Yang, L.; Chen, J.; Zhang, Z. Oxidative Cascade Iodocyclization of 1,n-Dienes: Synthesis of Iodinated Benzo[b]azepine and Benzo[b]azocine Derivatives. The Journal of organic chemistry 2024, 89, 6405–6415. doi:10.1021/acs.joc.4c00438
• Pothireddy, M.; Chatterjee, R.; Penke, V. B.; Dandela, R. I2/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles. Organic & biomolecular chemistry 2023, 21, 5521–5526. doi:10.1039/d3ob00771e
• Kumar, A.; Khatun, G. N.; Fernandes, R. A. TBAI-Catalyzed Regioselective Hydroxyperoxidation of 1-Aryl/Alkyl-1,3-dienes. Organic letters 2023, 25, 4313–4317. doi:10.1021/acs.orglett.3c01393
• Slathia, N.; Gupta, A.; Kapoor, K. K. I2/TBHP Reagent System: A Modern Paradigm for Organic Transformations**. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200460
• Xu, H.; Lou, X.; Xie, J.; Qin, Z.; He, H.; Gao, X. Regioselective Approach to β-Peroxyl Alcohols and Ethers from Alkenes. The Journal of organic chemistry 2022, 87, 9957–9968. doi:10.1021/acs.joc.2c00954
• Khan, A. T.; Mondal, S. α-Sulfenylation between 4-Hydroxydithiocoumarin and 1,3-Dicarbonyl Compounds: A Key Precursor for the Synthesis of New Pyrazole Derivatives. Synthesis 2022, 54, 4521–4528. doi:10.1055/s-0040-1719935
• Ajvazi, N.; Stavber, S. Electrophilic Iodination of Organic Compounds Using Elemental Iodine or Iodides: Recent Advances 2008–2021: Part I. Compounds 2022, 2, 3–24. doi:10.3390/compounds2010002
• Yao, H.; Hu, W.; Zhang, W. Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions. Molecules (Basel, Switzerland) 2020, 26, 105. doi:10.3390/molecules26010105
• Le, H. A. N.; Nguyen, L. H.; Nguyen, Q. N. B.; Nguyen, H. T.; Nguyen, K. Q.; Tran, P. H. Straightforward synthesis of benzoxazoles and benzothiazoles via photocatalytic radical cyclization of 2-substituted anilines with aldehydes. Catalysis Communications 2020, 145, 106120. doi:10.1016/j.catcom.2020.106120
• Yaremenko, I. A.; Radulov, P. S.; Medvedev, M. G.; Krivoshchapov, N. V.; Belyakova, Y. Y.; Korlyukov, A. A.; Ilovaisky, A. I.; Terent′ev, A. O.; Alabugin, I. V. How to Build Rigid Oxygen-Rich Tricyclic Heterocycles from Triketones and Hydrogen Peroxide: Control of Dynamic Covalent Chemistry with Inverse α-Effect. Journal of the American Chemical Society 2020, 142, 14588–14607. doi:10.1021/jacs.0c06294
• Chen, Y.; Ma, Y.; Li, L.; Cui, M.; Li, Z. Copper-catalyzed trifluoromethylthiolation-peroxidation of alkenes and allenes. Organic Chemistry Frontiers 2020, 7, 1837–1844. doi:10.1039/d0qo00533a
• Mondal, S.; Mahato, K.; Arora, N.; Kankane, D.; Singh, U. P.; Ali, S.; Khan, A. H.; Ghosh, S. S.; Khan, A. T. Newly synthesized 3-sulfenylindole derivatives from 4-hydroxydithiocoumarin using an oxidative cross dehydrogenative coupling reaction (OCDCR): potential lead molecules for antiproliferative activity. Organic & biomolecular chemistry 2020, 18, 4104–4113. doi:10.1039/d0ob00054j
• Su, Y.-L.; De Angelis, L.; Tram, L.; Yu, Y.; Doyle, M. P. Catalytic Oxidative Cleavage Reactions of Arylalkenes by tert-Butyl Hydroperoxide - A Mechanistic Assessment. The Journal of organic chemistry 2020, 85, 3728–3741. doi:10.1021/acs.joc.9b03346
• Shantharjun, B.; Rajeswari, R.; Vani, D.; Unnava, R.; Sridhar, B.; Reddy, K. R. Metal-Free, One-Pot Oxidative Triple Functionalization of Azaarenes with Methyl Arenes Mediated by Molecular Iodine/TBHP: Synthesis of N-Benzylated Iodo(iso)quinolinones. Asian Journal of Organic Chemistry 2019, 8, 2162–2171. doi:10.1002/ajoc.201900588
• Shen, J.; Xiao, B.; Hou, Y.; Wang, X.; Li, G.-Z.; Chen, J.; Wang, W.; Cheng, J.-B.; Yang, B.; Yang, S.-D. Cobalt(II)-Catalyzed Bisfunctionalization of Alkenes with Diarylphosphine Oxide and Peroxide. Advanced Synthesis & Catalysis 2019, 361, 5198–5209. doi:10.1002/adsc.201900873
• Bao, X.; Li, J.; Jiang, W.; Huo, C. Radical-Mediated Difunctionalization of Styrenes. Synthesis 2019, 51, 4507–4530. doi:10.1055/s-0039-1690987

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