Development of N-F fluorinating agents and their fluorinations: Historical perspective

Scholarly Works

• Lucas Kane, D.; Figula, B. C.; Balaraman, K.; Bertke, J. A.; Wolf, C. General alkyl fluoride functionalization via short-lived carbocation-organozincate ion pairs. Nature communications 2024, 15, 1866. doi:10.1038/s41467-024-45756-4
• McCann, S. D.; Dubina, S. H.; Kosjek, B.; Alwedi, E.; Behre, T.; Burgess, S. A.; Dal Poggetto, G.; DiRocco, D. A.; Hartmanshenn, C.; McMullen, J. P.; Padivitage, N.; Sun, A. C. Evolution of a Green and Sustainable Manufacturing Process for Belzutifan: Part 5─Chemoenzymatic Diastereoselective Fluorination/DKR. Organic Process Research & Development 2024, 28, 441–450. doi:10.1021/acs.oprd.3c00421
• Wang, C.-Q.; Feng, C. Applications of Nucleophilic Fluorine Sources in the Selective Fluorofunctionalization of Unsaturated Carbon-Carbon Bonds. Acta Chimica Sinica 2024, 82, 160. doi:10.6023/a23080373
• Wen, L.; Zou, Z.; Zhou, N.; Sun, C.; Xie, P.; Feng, P. Electrochemical Fluorination Functionalization of gem-Difluoroalkenes with CsF as a Fluorine Source: Access to Fluoroalkyl Building Blocks. Organic letters 2023, 26, 241–246. doi:10.1021/acs.orglett.3c03901
• Mizuta, S.; Tabira, M.; Shichiro, N.; Yamaguchi, T.; Ishihara, J.; Ishikawa, T. Reaction Mechanism and Origin of Stereoselectivity in the Fluorination and Trifluoromethylthiolation of 2‐Bromoamides with AgF and AgSCF3. European Journal of Organic Chemistry 2023, 27. doi:10.1002/ejoc.202301100
• Simon, K.; Znidar, D.; Glotz, G.; Dallinger, D.; Kappe, C. O. Investigations on the continuous flow generation of 2,6-dichloro-N-fluoropyridinium tetrafluoroborate using F2 gas. Journal of Flow Chemistry 2023, 13, 427–434. doi:10.1007/s41981-023-00291-z
• Adachi, A.; Hashimoto, T.; Aikawa, K.; Nozaki, K.; Okazoe, T. Difluorination of heterobenzylic C–H bonds with N-fluoro-N-(fluorosulfonyl)carbamate (NFC). Organic Chemistry Frontiers 2023, 10, 5362–5368. doi:10.1039/d3qo01162c
• Wang, M.; Rowshanpour, R.; Guan, L.; Ruskin, J.; Nguyen, P. M.; Wang, Y.; Zhang, Q. A.; Liu, R.; Ling, B.; Woltornist, R.; Stephens, A. M.; Prasad, A.; Dudding, T.; Lectka, T.; Pitts, C. R. Competition between C-C and C-H Bond Fluorination: A Continuum of Electron Transfer and Hydrogen Atom Transfer Mechanisms. Journal of the American Chemical Society 2023, 145, 22442–22455. doi:10.1021/jacs.3c06477
• Lee, T. C.; Tong, Y.; Fu, W. C. Advances in Continuous Flow Fluorination Reactions. Chemistry, an Asian journal 2023, 18, e202300723. doi:10.1002/asia.202300723
• Eichler, C.; Himmelstoß, M.; Plangger, R.; Weber, L. I.; Hartl, M.; Kreutz, C.; Micura, R. Advances in RNA Labeling with Trifluoromethyl Groups. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202302220. doi:10.1002/chem.202302220
• Borodkin, G. I. Mechanochemical synthesis of organohalogen compounds: a synthetic chemist's view. Успехи химии 2023, 92. doi:10.59761/rcr5091
• Eitzinger, A.; Reitz, J.; Antoni, P. W.; Mayr, H.; Ofial, A. R.; Hansmann, M. M. Mesoionische N‐Heterocyclische Olefine verschieben die obere Grenze der Nucleophilie‐Skala. Angewandte Chemie 2023, 135. doi:10.1002/ange.202309790
• Eitzinger, A.; Reitz, J.; Antoni, P. W.; Mayr, H.; Ofial, A. R.; Hansmann, M. M. Pushing the Upper Limit of Nucleophilicity Scales by Mesoionic N-Heterocyclic Olefins. Angewandte Chemie (International ed. in English) 2023, 62, e202309790. doi:10.1002/anie.202309790
• Paola, E. L.; Borum, A.; Podunavac, M.; Zakarian, A. Stereoselective Synthesis of α-Fluoro Carboxylic Acids by Ireland-Claisen Rearrangement. Organic letters 2023, 25, 6167–6171. doi:10.1021/acs.orglett.3c01276
• Ito, Y.; Adachi, A.; Aikawa, K.; Nozaki, K.; Okazoe, T. N-Fluorobenzenesulfonimide (NFSI) analogs with deprotectable substituents: synthesis of β-fluoroamines via catalytic aminofluorination of styrenes. Chemical communications (Cambridge, England) 2023, 59, 9195–9198. doi:10.1039/d3cc02292g
• Feng, Z.; Riemann, L.; Guo, Z.; Herrero, D.; Simon, M.; Golz, C.; Mata, R. A.; Alcarazo, M. Pentafluorocyclopropanation of (Hetero)arenes Using Sulfonium Salts: Applications in Late-Stage Functionalization. Angewandte Chemie (International ed. in English) 2023, 62, e202306764. doi:10.1002/anie.202306764
• Feng, Z.; Riemann, L.; Guo, Z.; Herrero, D.; Simon, M.; Golz, C.; Mata, R. A.; Alcarazo, M. Pentafluorocyclopropanation of (Hetero)arenes Using Sulfonium Salts: Applications in Late‐Stage Functionalization. Angewandte Chemie 2023, 135. doi:10.1002/ange.202306764
• Haufe, G. Selective Synthesis of Monofluorinated Compounds Applying Amine/HF Reagents. Chemical record (New York, N.Y.) 2023, 23, e202300140. doi:10.1002/tcr.202300140
• Shibata, N.; Cahard, D. N-Fluoro Ammonium Salts of Cinchona Alkaloids in Enantioselective Electrophilic Fluorination. Chemical record (New York, N.Y.) 2023, 23, e202300096. doi:10.1002/tcr.202300096
• Leibler, I. N.-M.; Gandhi, S. S.; Tekle-Smith, M. A.; Doyle, A. G. Strategies for Nucleophilic C(sp3)-(Radio)Fluorination. Journal of the American Chemical Society 2023, 145, 9928–9950. doi:10.1021/jacs.3c01824

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