Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

Scholarly Works

• Priyanka, C.; Madhu, D.; Gangadhar, P. S.; Giribabu, L.; Punna, N. Cross-conjugated vinylogous annulation of π-CF3-allyl Pd-complexes with 4-methyl-3-trifluoroacetyl-quinolones. Chemical communications (Cambridge, England) 2024, 60, 12233–12236. doi:10.1039/d4cc03953j
• Bai, M.; Zhang, L.; Liu, L.; Jia, C.; Zheng, Y.; Shang, H.; Sun, H.; Cui, B. Recent Advances in Trifluoromethylation of Olefins, Aldehydes, and Ketones. Current Organic Chemistry 2024, 28, 1229–1243. doi:10.2174/0113852728305885240506155446
• Veth, L.; Windhorst, A. D.; Vugts, D. J. Synthesis of 18F-labelled aryl trifluoromethyl ketones with improved molar activity. Chemical communications (Cambridge, England) 2024, 60, 6801–6804. doi:10.1039/d4cc01776e
• Kawai, K.; Kato, Y.; Araki, T.; Ikawa, S.; Usui, M.; Hoshiya, N.; Kishikawa, Y.; Escorihuela, J.; Shibata, N. Halo-perfluoroalkoxylation of gem-difluoroalkenes with short-lived alkali metal perfluoroalkoxides in triglyme. Chemical science 2024, 15, 9574–9581. doi:10.1039/d4sc02084g
• Chen, D.; Huang, L.; Liang, M.; Chen, X.; Cao, D.; Xiao, P.; Ni, C.; Hu, J. 1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6. Molecules (Basel, Switzerland) 2024, 29, 2905. doi:10.3390/molecules29122905
• Jana, S.; Telu, S.; Jakobsson, J. E.; Yang, B. Y.; Pike, V. W. Copper(I)-free syntheses of [11C/18F]trifluoromethyl ketones from alkyl or aryl esters and [11C/18F]fluoroform. Chemical communications (Cambridge, England) 2024, 60, 4589–4592. doi:10.1039/d4cc00465e
• Karuo, Y.; Tarui, A.; Sato, K.; Kawai, K.; Omote, M. Reactions Using Freons and Halothane as Halofluoroalkyl/Halofluoroalkenyl Building Blocks. Chemical record (New York, N.Y.) 2023, 23, e202300029. doi:10.1002/tcr.202300029
• Zhou, J.; Zhao, Z.; Shibata, N. Transition-metal-free silylboronate-mediated cross-couplings of organic fluorides with amines. Nature communications 2023, 14, 1847. doi:10.1038/s41467-023-37466-0
• 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
• Lee, H.-J.; Joo, J.-U.; Yim, S.-J.; Kim, D.-P.; Kim, H. Ex-situ generation and synthetic utilization of bare trifluoromethyl anion in flow via rapid biphasic mixing. Nature communications 2023, 14, 1231. doi:10.1038/s41467-022-35611-9
• Leadbeater, N. E.; Politano, F.; Brydon, W. P. Oxidation of α-Trifluoromethyl and Nonfluorinated Secondary Alcohols to Ketones Using a Nitroxide Catalyst. Synthesis 2023, 55, 1517–1524. doi:10.1055/s-0042-1752398
• Luo, Z.; Cahard, D.; Tsui, G. C. Using fluoroform in trifluoromethylation reactions. Journal of Fluorine Chemistry 2023, 266, 110092. doi:10.1016/j.jfluchem.2023.110092
• Li, F.; Ding, H.; Li, C. Hydrotrifluoromethylation of Alkenes with a Fluoroform-Derived Trifluoromethylboron Complex. Acta Chimica Sinica 2023, 81, 577. doi:10.6023/a23040127
• Sumii, Y.; Iwasaki, H.; Fujihira, Y.; Mahmoud, E. M.; Adachi, H.; Kagawa, T.; Cahard, D.; Shibata, N. KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N-Sulfinylimines Using HFC-125. The Journal of organic chemistry 2022, 87, 15806–15819. doi:10.1021/acs.joc.2c01821
• Fujihira, Y.; Iwasaki, H.; Sumii, Y.; Adachi, H.; Kagawa, T.; Shibata, N. Continuous-Flow Synthesis of Perfluoroalkyl Ketones via Perfluoroalkylation of Esters Using HFC-23 and HFC-125 under a KHMDS–Triglyme System. Bulletin of the Chemical Society of Japan 2022, 95, 1396–1406. doi:10.1246/bcsj.20220162
• Sheldon, D. J.; Crimmin, M. R. Repurposing of F-gases: challenges and opportunities in fluorine chemistry. Chemical Society reviews 2022, 51, 4977–4995. doi:10.1039/d1cs01072g
• Ono, M.; Sumii, Y.; Fujihira, Y.; Kagawa, T.; Mimura, H.; Shibata, N. Pentafluoroethylation of Carbonyl Compounds Using HFC-125 in a Flow Microreactor System. The Journal of organic chemistry 2021, 86, 14044–14053. doi:10.1021/acs.joc.1c00728

Explore citations to this article at