Hypervalent iodine(III)-induced methylene acetoxylation of 3-oxo-N-substituted butanamides

Scholarly Works

• Kumar, R.; Deepak; Jain, N. 1O2 and Base Assisted Oxidative Conversion of β-Enaminoesters to α-Acyloxy-β-ketoesters under Visible Light Irradiation. The Journal of organic chemistry 2024, 89, 14472–14482. doi:10.1021/acs.joc.4c01994
• Elsberg, J. G. D.; Borowski, T.; Reinheimer, E. W.; Berreau, L. M. Anion- and Water-facilitated Oxidative Carbon-Carbon Bond Cleavage and Diketonate Carboxylation in Cu(II) Chlorodiketonate Complexes. Inorganica chimica acta 2024, 571, 122203. doi:10.1016/j.ica.2024.122203
• Montgomery, C. A.; Jameel, I.; Cuzzucoli, F.; Chidley, T.; Hopkins, W. S.; Murphy, G. K. σ-Holes in Iodonium Ylides: Halogen-Bond Activation of Carboxylic Acids, Phenols and Thiophenols May Enable Their X-H Insertion Reactions. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202202029. doi:10.1002/chem.202202029
• Aslanoglu, F. Design of 1‐(2‐pyrrolidinone)‐butane‐1,3‐dione derivatives and acetoxylation of these compound's methylene via hypervalent iodine (III). Journal of Heterocyclic Chemistry 2022, 59, 1660–1663. doi:10.1002/jhet.4482
• Zhupeng, G.; Kai, X.; Xuetao, X.; Yating, Z.; Daoyong, Z. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents. Chinese Journal of Organic Chemistry 2022, 42, 3766. doi:10.6023/cjoc202205031
• Li, W.; Zheng, Y.; Qu, E.; Bai, J.; Deng, Q. β-Keto Amides: A Jack-of-All-Trades Building Block in Organic Chemistry. European Journal of Organic Chemistry 2021, 2021, 5151–5192. doi:10.1002/ejoc.202100692
• Indukuri, D. R.; Potuganti, G. R.; Nanubolu, J. B.; Alla, M. Synthesis of Dihydropyrrole Derivatives by Oxidative Functionalization of 2-Amino-4H-Chromenes Using Hypervalent Iodine Reagents. Synlett 2021, 32, 1109–1116. doi:10.1055/a-1500-6863
• Bityukov, O. V.; Matveeva, O. K.; Vil, V. A.; Kokorekin, V. A.; Nikishin, G. I.; Terent'ev, A. O. Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids. The Journal of organic chemistry 2019, 84, 1448–1460. doi:10.1021/acs.joc.8b02791
• Zhang, Z.; Gao, X.; Yu, H.; Zhang, G.; Liu, J. Copper‐Catalysed (Diacetoxyiodo)benzene‐Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides. Advanced Synthesis & Catalysis 2018, 360, 3406–3411. doi:10.1002/adsc.201800616
• Wang, Y.; Gao, Q.; Li, N.; Yifan, C.; Jingwen, C.; Gao, F.; Meng, Q. High-efficiency α-benzoyloxylation and hydroxylation of β-keto amides by phase transfer catalysis. Tetrahedron 2018, 74, 4126–4133. doi:10.1016/j.tet.2018.06.026
• Rao, C. B.; Yuan, J.; Zhang, Q.; Zhang, R.; Zhang, N.; Fang, J.; Dong, D. Iodosobenzene-Mediated α-Acyloxylation of 1,3-Dicarbonyl Compounds with Carboxylic Acids and Insight into the Reaction Mechanism. The Journal of organic chemistry 2018, 83, 2904–2911. doi:10.1021/acs.joc.8b00114
• Kato, T.; Yasui, K.; Odagi, M.; Nagasawa, K. Guanidinium Hydroiodide/Cumene Hydroperoxide-Mediated Intermolecular Oxidative Coupling Reaction of β–Ketoamides with Oxindoles. Advanced Synthesis & Catalysis 2017, 359, 2881–2889. doi:10.1002/adsc.201700266
• Bityukov, O. V.; Vil, V. A.; Merkulova, V. M.; Nikishin, G. I.; Terent'ev, A. O. Silica gel mediated oxidative C–O coupling of β-dicarbonyl compounds with malonyl peroxides in solvent-free conditions. Pure and Applied Chemistry 2017, 90, 7–20. doi:10.1515/pac-2017-0312
• Sasano, Y.; Yasuda, N.; Maeda, H. Negatively Charged π-Electronic Systems by Deprotonation of Hydroxy-Substituted Dipyrrolyldiketone Boron Complexes. Chemistry, an Asian journal 2016, 11, 3423–3429. doi:10.1002/asia.201601205
• Tan, L.; Liu, W.; Zhou, P.; Chen, C.; Zhang, Q. Regioselective synthesis of anilines and β-dibrominated acetamides from N-aryl acetoacetamides mediated by Cu(I) salts. Journal of Saudi Chemical Society 2016, 20, 220–226. doi:10.1016/j.jscs.2014.03.004
• Terent'ev, A. O.; Vil, V. A.; Gorlov, E. S.; Nikishin, G. I.; Pivnitsky, K. K.; Adam, W. Lanthanide-Catalyzed Oxyfunctionalization of 1,3-Diketones, Acetoacetic Esters, And Malonates by Oxidative C-O Coupling with Malonyl Peroxides. The Journal of organic chemistry 2016, 81, 810–823. doi:10.1021/acs.joc.5b02233
• Chen, C.; Tan, L.; Zhou, P. Approach for the synthesis of N-phenylamides from β-ketobutylanilides using dimethylformamide and dimethylacetamide as the acyl donors. Journal of Saudi Chemical Society 2015, 19, 327–333. doi:10.1016/j.jscs.2014.05.005
• Wang, Z.; Bi, X.; Liang, Y.; Liao, P.; Dong, D. A copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarbonyl compounds to carboxylic acids with the assistance of isocyanide. Chemical communications (Cambridge, England) 2014, 50, 3976–3978. doi:10.1039/c4cc00402g
• Tan, L.; Zhou, P.; Chen, C.; Liu, W. An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P2O5 and catalyzed by zinc bromide. Beilstein journal of organic chemistry 2013, 9, 2681–2687. doi:10.3762/bjoc.9.304
• Yuan, Y.; Yang, R.; Zhang-Negrerie, D.; Wang, J.; Du, Y.; Zhao, K. One-Pot Synthesis of 3-Hydroxyquinolin-2(1H)-ones from N-Phenylacetoacetamide via PhI(OCOCF3)2-Mediated α-Hydroxylation and H2SO4-Promoted Intramolecular Cyclization. The Journal of organic chemistry 2013, 78, 5385–5392. doi:10.1021/jo400541s

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