CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF₃SO₂Cl

Scholarly Works

• Sumran, G.; Jain, N.; Kumar, P.; Aggarwal, R. Trifluoromethyl-β-dicarbonyls as Versatile Synthons in Synthesis of Heterocycles. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202303599. doi:10.1002/chem.202303599
• Tsuruta, T.; Spinnato, D.; Moon, H. W.; Leutzsch, M.; Cornella, J. Bi-Catalyzed Trifluoromethylation of C(sp2)-H Bonds under Light. Journal of the American Chemical Society 2023, 145, 25538–25544. doi:10.1021/jacs.3c10333
• Yang, C.; Liu, D.; Li, L.; Zhang, Y.; Xia, X.; Jiang, H.; Cheng, W. Light‐induced FeCl3‐catalyzed selective benzyl C−H chlorination with trifluoromethanesulfonyl chloride. Advanced Synthesis & Catalysis 2023, 365, 4144–4149. doi:10.1002/adsc.202300672
• Yang, L.; Wang, S.; Liang, F.; Han, Y.; Li, Y.; Shan, D.; Liu, L.; Wang, Q.; Zhu, D. Direct transfer of a trifluoromethylsulfinyl group by a general reagent N-trifluoromethylsulfinylphthalimide under a catalytic or stoichiometric Lewis acid or Lewis base. Organic Chemistry Frontiers 2023, 10, 4368–4380. doi:10.1039/d3qo00908d
• Yang, Y.; Miraghaee, S.; Pace, R.; Umemoto, T.; Hammond, G. B. Preparation and Reactivity Study of a Versatile Trifluoromethylthiolating Agent: S-Trifluoromethyl Trifluoromethanesulfonothioate (TTST). Angewandte Chemie (International ed. in English) 2023, 62, e202306095. doi:10.1002/anie.202306095
• Yang, Y.; Miraghaee, S.; Pace, R.; Umemoto, T.; Hammond, G. B. Preparation and Reactivity Study of a Versatile Trifluoromethylthiolating Agent: S‐Trifluoromethyl Trifluoromethanesulfonothioate (TTST). Angewandte Chemie 2023, 135. doi:10.1002/ange.202306095
• Zheng, L.; Qiu, X.; Xiao, Z.; Ma, X.; Gao, T.; Zhou, X.; Wang, Y.; Guo, Y.; Chen, Q.-Y.; Liu, C. Deoxygenation of ClSO2CF2COOMe with Triphenylphosphine for the Metal-Free Direct Electrophilic Difluoroalkylthiolation of Various Heterocycles. The Journal of organic chemistry 2023, 88, 7518–7524. doi:10.1021/acs.joc.3c00342
• Levin, V. V.; Dilman, A. D. Visible-Light Promoted Radical Fluoroalkylation of O- and N-Substituted Alkenes. Chemical record (New York, N.Y.) 2023, 23, e202300038. doi:10.1002/tcr.202300038
• Kawamura, S.; Barrio, P.; Fustero, S.; Escorihuela, J.; Han, J.; A. Soloshonok, V.; Sodeoka, M. Evolution and Future of Hetero‐ and Hydro‐Trifluoromethylations of Unsaturated C−C Bonds. Advanced Synthesis & Catalysis 2023, 365, 398–462. doi:10.1002/adsc.202201268
• Storozhenko, O. A.; Festa, A. A.; Zolotareva, V. A.; Rybakov, V. B.; Varlamov, A. V.; Voskressensky, L. G. Photoredox-Catalyzed Chlorotrifluoromethylation of Arylallenes: Synthesis of a Trifluoromethyl Building Block. Organic letters 2023, 25, 438–442. doi:10.1021/acs.orglett.2c04214
• 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
• Xu, X.; Qing, F. doi:10.1002/9783527831883.ch36
• Lemmens, V.; Vos, C.; Bugaev, A. L.; Vercammen, J.; Van Velthoven, N.; Gascon, J.; De Vos, D. E. Ru-Bipyridine Entrapped in the Supercages of EMC-1 Faujasite as Catalyst for the Trifluoromethylation of Arenes. ACS applied materials & interfaces 2021, 14, 971–977. doi:10.1021/acsami.1c19655
• Vytla, D.; Kaliyaperumal, K.; Velayuthaperumal, R.; Shaw, P.; Gautam, R.; Mathur, A.; Roy, A. Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives. Synthesis 2021, 54, 667–682. doi:10.1055/s-0040-1720921
• Lin, S.; Cui, J.; Chen, Y.; Li, Y. Copper-Catalyzed Direct Cycloaddition of Imidazoles and Alkenes to Trifluoromethylated Tricyclic Imidazoles. The Journal of organic chemistry 2021, 86, 15768–15776. doi:10.1021/acs.joc.1c01832
• Kim, B.; Park, J.; Cho, C.-W. Synthesis of N-Trifluoromethanesulfinyl Ketimines by Cascade Trifluoromethylthiolation/Rearrangement of Ketoximes. Organic letters 2021, 23, 4603–4607. doi:10.1021/acs.orglett.1c01338
• Chun, J.; Zhang, H.; Meng, F.; Guo, K.; Cao, S.; Fang, Q.; Li, J.; Zhu, Y. Visible-Light Photoredox-Catalyzed Tandem Trifluoro-methylation/Cyclization/Remote Oxidation of 1,6-Dienes: Access to CF3-Containing Five-Membered Heterocycles. Advanced Synthesis & Catalysis 2020, 363, 751–756. doi:10.1002/adsc.202001272
• Wu, W.; Chen, Q.; Tian, Y.; Xu, Y.; Huang, Y.; You, Y.; Weng, Z. Synthesis of polysubstituted 5-trifluoromethyl isoxazoles via denitrogenative cyclization of vinyl azides with trifluoroacetic anhydride. Organic Chemistry Frontiers 2020, 7, 1878–1883. doi:10.1039/d0qo00243g
• Koike, T.; Akita, M. Recent progress in photochemical radical di- and mono-fluoromethylation. Organic & biomolecular chemistry 2019, 17, 5413–5419. doi:10.1039/c9ob00734b
• Chen, L.; Wu, L.; Duan, W.; Wang, T.; Li, L.; Zhang, K.; Zhu, J.; Peng, Z.; Xiong, F. Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates with CF3SO2Cl To Construct 3-Trifluoromethyl Coumarin Derivatives. The Journal of organic chemistry 2018, 83, 8607–8614. doi:10.1021/acs.joc.8b00581

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