CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

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• Lu, W.; Chen, K.; Lv, L.; Li, Z. Palladium-Catalyzed Cascade Cross-Coupling/Retro-Claisen Reaction of CF3-Substituted β-Diketones with gem-Difluorocyclopropanes. The Journal of organic chemistry 2025, 90, 13323–13332. doi:10.1021/acs.joc.5c01788
• Longuet, M.; Naullet, F.; Pérochon, A.; Martin-Mingot, A.; Guégan, F.; Michelet, B.; Thibaudeau, S. Regulating the Acidity of HF/Pyridine Media to Control the Chemodivergent Fluoro- and Hydro-Heteroalkylation of Olefins. Journal of the American Chemical Society 2025, 147, 29079–29087. doi:10.1021/jacs.5c07526
• Luković, E.; Zhu, Y.; Zhang, Y.; Genualdi, J. R.; Sang, S.; Emala, C. W. Design and Evaluation of Novel Ginger 6-Shogaol-Inspired Phospholipase C Inhibitors to Enhance β-Agonist-Induced Relaxation in Human Airway Smooth Muscle. Journal of medicinal chemistry 2025, 68, 12626–12640. doi:10.1021/acs.jmedchem.5c00378
• Shi, H.; Ma, J.; Marek, I.; Zhang, F. Fe‐Catalyzed Stereospecific Intramolecular Friedel–Crafts‐type Reaction of Fluoroalkyl Cyclopropyl Carbinols via Non‐classical Carbocation. Advanced Synthesis & Catalysis 2025, 367. doi:10.1002/adsc.202500242
• Gnanasekaran, P.; Cheng, Y.; Wu, J.; Peng, J.; Chen, C.; Chang, R.; Vailassery, J.; Sun, S.; Chang, C.; Chang, Y. J. Shamrock‐Shaped D2–A–Cz Materials Featuring Trifluoromethyl Carbazole and Pyrimidine: a Tailored Host for Green Phosphorescent OLEDs. Advanced Materials Technologies 2025, 10. doi:10.1002/admt.202401607
• Xiao, W.; Xiao, L.; Guo, D.; Zhu, Z.; Cheng, Z. Detrifluoromethylamination of trifluoromethyl pyrazolo[1,5-a]pyrimidins enabled by unusual C-CF3 bond cleavage. Tetrahedron 2024, 167, 134216. doi:10.1016/j.tet.2024.134216
• Giri, R.; Kissling, M.; Zhilin, E.; Fernandes, A. J.; Ordan, Q. E. L.; Katayev, D. Divergent Synthesis of Trifluoromethyl Ketones via Photoredox Activation of Halotrifluoroacetones. Helvetica Chimica Acta 2024, 107. doi:10.1002/hlca.202400125
• Steiner, S.; Shafiq, Z. M.; Nitzer, A.; Hollenwäger, D.; Kornath, A. J. HF-addition to haloacetyl fluorides in superacidic media. New Journal of Chemistry 2024, 48, 13846–13853. doi:10.1039/d4nj02884h
• Kolbunova, A. V.; Klyukin, I. N.; Novikov, A. S.; Nelyubin, A. V.; Zhdanov, A. P.; Kubasov, A. S.; Selivanov, N. A.; Bykov, A. Y.; Zhizhin, K. Y.; Kuznetsov, N. T. Carboxonium derivatives based on closo-dodecaborate anions [1,2-B12H10O2CR]−: synthesis and molecular orbital analysis. New Journal of Chemistry 2024, 48, 8361–8370. doi:10.1039/d4nj01048e
• Teng, Y.; Yu, X.; Shang, D.; Wang, Z.; Rao, W. Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF3-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles. The Journal of organic chemistry 2024, 89, 1147–1159. doi:10.1021/acs.joc.3c02331
• Sokolov, V. A.; Golushko, A. A.; Boyarskaya, I. A.; Vasilyev, A. V. Cyclization of 1-aryl-4,4,4-trichlorobut-2-en-1-ones into 3-trichloromethylindan-1-ones in triflic acid. Beilstein journal of organic chemistry 2023, 19, 1460–1470. doi:10.3762/bjoc.19.105
• Feng, L.; Teng, Y.; Yu, X.; Wang, Z.; Rao, W. Brønsted Acid-Catalyzed Dehydrative Nazarov-Type Cyclization/C2-N1 Cleavage Cascade of Perfluoroalkylated 3-Indolyl(2-benzothienyl)methanols. Organic letters 2023, 25, 4956–4961. doi:10.1021/acs.orglett.3c01503
• Wijaya, F.; Woo, S.; Kim, S.; Chon, M.; Kim, J.; Lee, H.; Kim, H.; Lee, H.; Shin, D.; Bae, B. Sulfonated Polyphenylene-Based Multiblock Membranes with Fluorine Moiety for Fuel Cell Applications. International Journal of Energy Research 2023, 2023, 1–13. doi:10.1155/2023/5562126
• Mestre, J.; Bascuas, I.; Bernús, M.; Castillón, S.; Boutureira, O. Stereoselective access to 2-deoxy-2-trifluoromethyl sugar mimetics by trifluoromethyl-directed 1,2-trans glycosylation. Organic Chemistry Frontiers 2023, 10, 2405–2415. doi:10.1039/d3qo00274h
• Shershnev, I. A.; Boyarskaya, I. A.; Vasilyev, A. V. 5,5,5-Trichloropent-3-en-one as a Precursor of 1,3-Bi-centered Electrophile in Reactions with Arenes in Brønsted Superacid CF3SO3H. Synthesis of 3-Methyl-1-trichloromethylindenes. Molecules (Basel, Switzerland) 2022, 27, 6675. doi:10.3390/molecules27196675
• Vayer, M.; Mayer, R. J.; Moran, J.; Lebœuf, D. Leveraging the Hydroarylation of α-(Trifluoromethyl)styrenes to Access Trifluoromethylated All-Carbon Quaternary Centers. ACS Catalysis 2022, 12, 10995–11001. doi:10.1021/acscatal.2c03330
• Wang, X.; Pan, S.; Luo, Q.; Wang, Q.; Ni, C.; Hu, J. Controllable Single and Double Difluoromethylene Insertions into C-Cu Bonds: Copper-Mediated Tetrafluoroethylation and Hexafluoropropylation of Aryl Iodides with TMSCF2H and TMSCF2Br. Journal of the American Chemical Society 2022, 144, 12202–12211. doi:10.1021/jacs.2c03104
• Kochurin, M. A.; Ismagilova, A. R.; Zakusilo, D. N.; Khoroshilova, O. V.; Boyarskaya, I. A.; Vasilyev, A. V. Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species. New Journal of Chemistry 2022, 46, 12041–12053. doi:10.1039/d2nj01828d
• Han, X.; Liu, X.; Bao, Y.; Song, H.; Zhao, Y.-R.; Wang, X.; Zhang, J.; Liu, L.; Duan, X.-H.; Hu, J.; Hu, M. Water-promoted regio-selective trifluoromethylation of vinyl conjugated diazoacetates. Organic Chemistry Frontiers 2021, 9, 204–209. doi:10.1039/d1qo01654g
• Sang, J.; Feng, L.; Hu, R.; Chen, J.; Shang, D.; Qing, B.; Rao, W. Sc(OTf)3-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines. Organic letters 2021, 23, 7666–7671. doi:10.1021/acs.orglett.1c02932

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