Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

Scholarly Works

• Bains, O.; Jangra, R.; Kumar, A.; Kumar, R.; Kataria, R.; Sharma, P.; Kamal, R. HTIB-Driven cascade approach towards C-C bond formation: Synthetic, crystallographic and computational exploration of α-heteroaryl-β,β-ditosyloxy ketones. Journal of Molecular Structure 2025, 1351, 144103. doi:10.1016/j.molstruc.2025.144103
• Liu, N.; Cuan, X.; Li, H.; Duan, X. Progress in the Study of α-Functionalization of Enaminone. Chinese Journal of Organic Chemistry 2023, 43, 602. doi:10.6023/cjoc202207027
• 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
• Tarannum, S.; Chauhan, N.; Ghorai, M. K. Aziridines and 2H-Azirines—Monocyclic. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 1–114. doi:10.1016/b978-0-12-409547-2.14954-6
• De, A.; Majee, A. Synthesis of Various Functionalized 2 H ‐azirines‐An Updated Library. Journal of Heterocyclic Chemistry 2021, 59, 422–448. doi:10.1002/jhet.4415
• Agafonova, A. V.; Smetanin, I. A.; Rostovskii, N. V.; Khlebnikov, A. F.; Novikov, M. S. Synthesis of 2-(2-Pyridyl)-2 H -azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines. Organic letters 2021, 23, 8045–8049. doi:10.1021/acs.orglett.1c03060
• Duan, X.; Li, H.; Li, W.; Wang, J.; Liu, N. NBS-Promoted C−H Amination of Enaminones for the Synthesis of N-Heterocycle Substituted Enaminones**. ChemistrySelect 2021, 6, 6478–6482. doi:10.1002/slct.202101726
• Kareem, R. T.; Azizi, B.; Asnaashariisfahani, M.; Ebadi, A. G.; Vessally, E. Vicinal halo-trifluoromethylation of alkenes. RSC advances 2021, 11, 14941–14955. doi:10.1039/d0ra06872a
• Terashima, K.; Kawasaki-Takasuka, T.; Yamazaki, T. Construction of fully substituted carbon centers containing a heteroatom and a CF3 group via in situ generated p-quinone methides. Organic & biomolecular chemistry 2021, 19, 1305–1314. doi:10.1039/d0ob02469d
• Babaoglu, E.; Hilt, G. Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates Supported by Design of Experiments. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 8879–8884. doi:10.1002/chem.202001465
• Zhang, G.; Wang, Y.; Xu, J.; Sun, J.; Sun, F.; Zhang, Y.; Zhang, C.; Du, Y. A new hypervalent iodine(III/V) oxidant and its application to the synthesis of 2H-azirines. Chemical science 2019, 11, 947–953. doi:10.1039/c9sc05536c
• Cai, G.; Li, B.; Geng, X.; Zhou, Q.; Zhang, X.; Fan, X. Two birds with one stone: one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent. Green Chemistry 2019, 21, 5113–5117. doi:10.1039/c9gc02001b
• Khlebnikov, A. F.; Novikov, M. S.; Rostovskii, N. V. Advances in 2H-azirine chemistry: A seven-year update. Tetrahedron 2019, 75, 2555–2624. doi:10.1016/j.tet.2019.03.040

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