Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

Scholarly Works

• Huang, Y.; Huang, J.; Wang, P.; Liao, S. Photoredox Catalytic Two‐Component Radical β‐Fluoro‐Fluorosulfonamidation Reaction of Styrenes. European Journal of Organic Chemistry 2025. doi:10.1002/ejoc.202500172
• Shang, Z.; Pan, J.; Wang, Z.; Zhang, Z.; Wu, J. Transition‐Metal‐Free Radical Borylation Reactions. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202201379
• Luo, L.; Tang, S.; Wu, J.; Jin, S.; Zhang, H. Transition Metal-Free Aromatic C-H, C-N, C-S and C-O Borylation. Chemical record (New York, N.Y.) 2023, 23, e202300023. doi:10.1002/tcr.202300023
• Liu, Y.; Zeplichal, M.; Katzbach, S.; Wiesner, A.; Das, S.; Terfort, A.; Zharnikov, M. Aromatic self-assembled monolayers with pentafluoro-λ6-sulfanyl (−SF5) termination: Molecular organization and charge transport properties. Nano Research 2023, 16, 7991–8002. doi:10.1007/s12274-022-5350-8
• Ghosh, S.; Qu, Z.-W.; Roy, S.; Grimme, S.; Chatterjee, I. Photoredox Catalyzed Single C-F Bond Activation of Trifluoromethyl Ketones: A Solvent Controlled Divergent Access of gem-Difluoromethylene Containing Scaffolds. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202203428. doi:10.1002/chem.202203428
• Kordnezhadian, R.; Li, B.-Y.; Zogu, A.; Demaerel, J.; De Borggraeve, W. M.; Ismalaj, E. Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202201491. doi:10.1002/chem.202201491
• Ghosh, S.; Qu, Z.; Pradhan, S.; Ghosh, A.; Grimme, S.; Chatterjee, I. HFIP‐Assisted Single C−F Bond Activation of Trifluoromethyl Ketones using Visible‐Light Photoredox Catalysis. Angewandte Chemie 2021, 134. doi:10.1002/ange.202115272
• Chatterjee, I.; Ghosh, S.; Qu, Z.-W.; Pradhan, S.; Ghosh, A.; Grimme, S. HFIP-Assisted Single C-F Bond Activation of Trifluoromethyl Ketones using Visible-Light Photoredox Catalysis. Angewandte Chemie (International ed. in English) 2021, 61, e202115272. doi:10.1002/anie.202115272
• Yang, L.; Zhang, C.-P. Additive-Free Visible-Light-Mediated Hydro-/Deuterodediazoniation of Arenediazonium Tetrafluoroborates in THF/THF-d8. Asian Journal of Organic Chemistry 2021, 10, 2157–2160. doi:10.1002/ajoc.202100322
• Firth, J. D.; Hammarback, A.; Burden, T. J.; Eastwood, J. B.; Donald, J. R.; Horbaczewskyj, C.; McRobie, M.; Tramaseur, A.; Clark, I. P.; Towrie, M.; Robinson, A.; Krieger, J.-P.; Lynam, J. M.; Fairlamb, I. J. S. Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 3979–3985. doi:10.1002/chem.202004568
• Wang, M.; Shi, Z. Methodologies and Strategies for Selective Borylation of C–Het and C–C Bonds. Chemical reviews 2020, 120, 7348–7398. doi:10.1021/acs.chemrev.9b00384
• Dutta, S.; Saha, A. Aryldithiocarbamates as thiol alternatives in Cu-catalyzed C(aryl)-S coupling reactions using aryldiazonium tetrafluoroborate salts. Organic & biomolecular chemistry 2019, 17, 9360–9366. doi:10.1039/c9ob01976f
• Sumii, Y.; Sasaki, K.; Tsuzuki, S.; Shibata, N. Studies of Halogen Bonding Induced by Pentafluorosulfanyl Aryl Iodides: A Potential Group of Halogen Bond Donors in a Rational Drug Design. Molecules (Basel, Switzerland) 2019, 24, 3610. doi:10.3390/molecules24193610
• Donald, J. R.; Berrell, S. L. Radical cyanomethylation via vinyl azide cascade-fragmentation. Chemical science 2019, 10, 5832–5836. doi:10.1039/c9sc01370a
• Zhang, X.; Zhang, Z.; Xie, Y.; Jiang, Y.; Xu, R.-b.; Luo, Y.; Tao, C. Alcohol-Initiated Dediazoniation of Aryldiazonium Ions to Aryl Radicals: A Simple and Efficient Route to Arylboronates:. Journal of Chemical Research 2018, 42, 481–485. doi:10.3184/174751918x15362432558247
• Borosky, G. L.; Laali, K. K. A computational study of SF5-substituted carbocations. Journal of Fluorine Chemistry 2017, 197, 118–133. doi:10.1016/j.jfluchem.2017.04.002
• Laali, K. K. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd, 2016; pp 1–3. doi:10.1002/047084289x.rn02003
• Desroches, J.; Tremblay, A.; Paquin, J.-F. Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols. Organic & biomolecular chemistry 2016, 14, 8764–8780. doi:10.1039/c6ob01663d
• Berg, C.; Braun, T.; Laubenstein, R.; Braun, B. Palladium-mediated borylation of pentafluorosulfanyl functionalized compounds: the crucial role of metal fluorido complexes. Chemical communications (Cambridge, England) 2016, 52, 3931–3934. doi:10.1039/c5cc10219g
• Ajenjo, J.; Greenhall, M.; Zarantonello, C.; Beier, P. Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene. Beilstein journal of organic chemistry 2016, 12, 192–197. doi:10.3762/bjoc.12.21

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