Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

Scholarly Works

• Rizzo, C.; Amata, S.; Pibiri, I.; Pace, A.; Buscemi, S.; Palumbo Piccionello, A. FDA-Approved Fluorinated Heterocyclic Drugs from 2016 to 2022. International Journal of Molecular Sciences 2023, 24, 7728. doi:10.3390/ijms24097728
• Popov, A. V.; Kobelevskaya, V. A.; Borodin, N. I.; Zinchenko, S. V. α,β-Unsaturated CF3-ketones via secondary amine salts-catalyzed aldol condensation of 1,1,1-trufluoroacetone with aromatic and heteroaromatic aldehydes. Journal of Fluorine Chemistry 2023, 267, 110108. doi:10.1016/j.jfluchem.2023.110108
• Hall, J. R.; Blythe, I. M.; Sharninghausen, L. S.; Sanford, M. S. Copper-Mediated Fluoroalkylation of Aryl Bromides and Chlorides Enabled by Directing Groups. Organometallics 2023, 42, 543–546. doi:10.1021/acs.organomet.3c00066
• Wang, D.; Wan, X.; Zhou, Y.; Liu, J.; Cai, J.; Deng, G. Facile Synthesis of Fully Substituted 1,2,4‐Triazoles via [3+2] Cycloaddition of Nitrileimines with Amidine under Transition Metal‐Free Conditions. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202200674
• Zuo, Y.; Ye, X.; Jiang, D.; Zhou, S.; Yu, M.; He, G. Cu(I)‐Catalyzed Oxytrifluoromethylation of N ‐Boc‐Ynamides for the Construction of Trifluoromethylated Oxazolones. Advanced Synthesis & Catalysis 2022, 364, 4146–4151. doi:10.1002/adsc.202200971
• Deolka, S.; Govindarajan, R.; Vasylevskyi, S.; Roy, M. C.; Khusnutdinova, J. R.; Khaskin, E. Ligand-free nickel catalyzed perfluoroalkylation of arenes and heteroarenes. Chemical science 2022, 13, 12971–12979. doi:10.1039/d2sc03879j
• Yan, Z.-H.; Li, W.-C.; Wu, Y.-H.; Yan, Q.-B.; Wei, Z.-L.; Liao, W.-W. Electrochemical cyclization of N-cyanamide alkenes with CF3SO2Na to access C,N-(bis)trifluoromethylated cyclic amidines and related compounds. Organic Chemistry Frontiers 2022, 9, 5912–5920. doi:10.1039/d2qo01323a
• Nair, A. S.; Singh, A. K.; Kumar, A.; Kumar, S.; Sukumaran, S.; Koyiparambath, V. P.; Pappachen, L. K.; Rangarajan, T. M.; Kim, H.; Mathew, B. FDA-Approved Trifluoromethyl Group-Containing Drugs: A Review of 20 Years. Processes 2022, 10, 2054. doi:10.3390/pr10102054
• Amii, H. Perfluoroalkyl Compounds for Industrial and Other Applications. Perfluoroalkyl Substances; The Royal Society of Chemistry, 2022; pp 66–112. doi:10.1039/9781839167591-00066
• Mudshinge, S. R.; Hammond, G. B.; Umemoto, T. Synthesis and applications of S-(trifluoromethyl)-2,8-bis(trifluoromethoxy)dibenzothiophenium triflate (Umemoto reagent IV). Journal of fluorine chemistry 2022, 261-262, 110015. doi:10.1016/j.jfluchem.2022.110015
• Jain, R.; Dhillon, N. S.; Farquhar, E. R.; Wang, B.; Li, X.; Kiselar, J.; Chance, M. R. Multiplex Chemical Labeling of Amino Acids for Protein Footprinting Structure Assessment. Analytical chemistry 2022, 94, 9819–9825. doi:10.1021/acs.analchem.2c01640
• Yao, R.; Ling, Y.; Chen, W.; Lu, L.; Shen, Q. Kilogram-Scale Preparation of the Easily Available, Low-Cost Electrophilic Trifluomethylating Reagent YlideFluor. Organic Process Research & Development 2022, 26, 299–306. doi:10.1021/acs.oprd.1c00381
• Hirabayashi, K.; Nakashizuka, M.; Shimizu, T. Synthesis, Structure, and Properties of Unsaturated Thiacrown Ethers Possessing Sulfonium Groups. Chemistry, an Asian journal 2022, 17, e202101329. doi:10.1002/asia.202101329
• Malischewski, M. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering - Very High Oxidation States in Organometallic Chemistry. Comprehensive Organometallic Chemistry IV; Elsevier, 2022; pp 109–134. doi:10.1016/b978-0-12-820206-7.00004-4
• Baishya, G.; Dutta, N. B. Recent Advances in Direct C−H Trifluoromethylation of N‐Heterocycles. ChemistrySelect 2021, 6, 13384–13408. doi:10.1002/slct.202103407
• Zhao, W.-W.; Shao, Y.-C.; Wang, A.-N.; Huang, J.-L.; He, C.-Y.; Cui, B.; Wan, N.-W.; Chen, Y.; Han, W. Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition. Organic letters 2021, 23, 9256–9261. doi:10.1021/acs.orglett.1c03603
• Zhang, H.; Shen, Q. (1S)-(−)-N-Monofluoromethylthio-7,7-dichloro-2,10-camphorsultam: An optically pure reagentfor asymmetric monofluoromethylthiolation. Tetrahedron 2021, 101, 132508. doi:10.1016/j.tet.2021.132508
• Teng, S.; Meng, L.; Xu, B.; Tu, G.; Wu, P.; Liao, Z.; Tan, Y.; Guo, J.; Zeng, J.; Wan, Q. Togni-II Reagent Mediated Selective Hydrotrifluoromethylation and Hydrothiolation of Alkenes†. Chinese Journal of Chemistry 2021, 39, 3429–3434. doi:10.1002/cjoc.202100464
• Zhou, J.; Zhao, Z.; Shibata, N. Silylboronate-Mediated Defluorosilylation of Aryl Fluorides with or without Ni-Catalyst. Frontiers in chemistry 2021, 9, 771473. doi:10.3389/fchem.2021.771473
• Wang, Y.; Velkos, G.; Israel, N. J.; Rosenkranz, M.; Büchner, B.; Liu, F.; Popov, A. A. Electrophilic Trifluoromethylation of Dimetallofullerene Anions en Route to Air-Stable Single-Molecule Magnets with High Blocking Temperature of Magnetization. Journal of the American Chemical Society 2021, 143, 18139–18149. doi:10.1021/jacs.1c07021

Explore citations to this article at