Stereochemical outcomes of C–F activation reactions of benzyl fluoride

Scholarly Works

• Sakaguchi, D.; Shimono, M.; Gotoh, H. Analysis of Asymmetric Reduction of Ketones Using Three-Dimensional Electronic States. The journal of physical chemistry. A 2025, 129, 8945–8958. doi:10.1021/acs.jpca.5c03510
• Hamel, J.; Ferlet, R.; Chabaud, L.; Paquin, J. doi:10.1002/9780470682531.pat1005
• Garg, A.; Haswell, A.; Hopkinson, M. N. C-F Bond Insertion: An Emerging Strategy for Constructing Fluorinated Molecules. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202304229. doi:10.1002/chem.202304229
• Kitahara, T.; Tagami, Y.; Haga, Y.; Fustero, S.; Sugiishi, T.; Amii, H. Alkylation and silylation of α-fluorobenzyl anion intermediates. Organic & biomolecular chemistry 2023, 21, 9210–9215. doi:10.1039/d3ob01586f
• Bertrand, X.; Pucheault, M.; Chabaud, L.; Paquin, J.-F. Synthesis of Tertiary Fluorides through an Acid-Mediated Deoxyfluorination of Tertiary Alcohols. The Journal of organic chemistry 2023, 88, 14527–14539. doi:10.1021/acs.joc.3c01558
• Ishitani, H.; Kawase, T.; Das, A.; Kobayashi, S. Catalytic hydrogenative dechlorination reaction for efficient synthesis of a key intermediate of SDHI fungicides under continuous-flow conditions. Catalysis Science & Technology 2023, 13, 3282–3291. doi:10.1039/d3cy00182b
• Garg, A.; Gerwien, N. J.; Fasting, C.; Charlton, A.; Hopkinson, M. N. Formal Insertion of Alkenes Into C(sp3)−F Bonds Mediated by Fluorine‐Hydrogen Bonding. Angewandte Chemie 2023, 135. doi:10.1002/ange.202302860
• Garg, A.; Gerwien, N. J.; Fasting, C.; Charlton, A.; Hopkinson, M. N. Formal Insertion of Alkenes Into C(sp3 )-F Bonds Mediated by Fluorine-Hydrogen Bonding. Angewandte Chemie (International ed. in English) 2023, 62, e202302860. doi:10.1002/anie.202302860
• Yeganeh-Salman, A.; Elser, I.; Bamford, K. L.; Ebanks, D.; Stephan, D. W. Probing B-X to B-H conversions and applications in C-F bond activation catalysis. Dalton transactions (Cambridge, England : 2003) 2022, 51, 17962–17966. doi:10.1039/d2dt03588j
• Nielsen, M. M.; Pedersen, C. M. Vessel effects in organic chemical reactions; a century-old, overlooked phenomenon. Chemical science 2022, 13, 6181–6196. doi:10.1039/d2sc01125e
• Ai, H.-J.; Ma, X.; Song, Q.; Wu, X.-F. C-F bond activation under transition-metal-free conditions. Science China Chemistry 2021, 64, 1630–1659. doi:10.1007/s11426-021-1040-2
• Vulpetti, A.; Dalvit, C. Hydrogen Bond Acceptor Propensity of Different Fluorine Atom Types: An Analysis of Experimentally and Computationally Derived Parameters. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 8764–8773. doi:10.1002/chem.202100301
• Houle, C.; Savoie, P. R.; Davies, C.; Jardel, D.; Champagne, P. A.; Bibal, B.; Paquin, J.-F. Thiourea-Catalyzed C-F Bond Activation: Amination of Benzylic Fluorides. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 10620–10625. doi:10.1002/chem.202001905
• Nielsen, M. M.; Qiao, Y.; Wang, Y.; Pedersen, C. Vessel Effect in C–F Bond Activation Prompts Revised Mechanism and Reveals an Autocatalytic Glycosylation. European Journal of Organic Chemistry 2020, 2020, 140–144. doi:10.1002/ejoc.201901755
• Pryyma, A.; Bu, Y. J.; Wai, Y.; Patrick, B. O.; Perrin, D. M. Synthesis and Activation of Bench-Stable 3a-Fluoropyrroloindolines as Latent Electrophiles for the Synthesis of C-2-Thiol-Substituted Tryptophans and C-3a-Substituted Pyrroloindolines. Organic letters 2019, 21, 8234–8238. doi:10.1021/acs.orglett.9b02972
• Guo, J.; Bamford, K. L.; Stephan, D. W. 9-Borabicyclo[3.3.l]nonane-induced Friedel–Crafts benzylation of arenes with benzyl fluorides. Organic & biomolecular chemistry 2019, 17, 5258–5261. doi:10.1039/c9ob00912d
• Hamel, J.-D.; Paquin, J.-F. Activation of C–F bonds α to C–C multiple bonds. Chemical communications (Cambridge, England) 2018, 54, 10224–10239. doi:10.1039/c8cc05108a

Explore citations to this article at