Amine–borane complex-initiated SF5Cl radical addition on alkenes and alkynes

Audrey Gilbert, Pauline Langowski, Marine Delgado, Laurent Chabaud, Mathieu Pucheault and Jean-François Paquin
Beilstein J. Org. Chem. 2020, 16, 3069–3077. https://doi.org/10.3762/bjoc.16.256

Supporting Information

Supporting Information File 1: General information, synthetic procedures, additional optimization results, NMR spectra for known compounds (1H, 19F) and full characterization of all new compounds.
Format: PDF Size: 2.5 MB Download

Cite the Following Article

Amine–borane complex-initiated SF5Cl radical addition on alkenes and alkynes
Audrey Gilbert, Pauline Langowski, Marine Delgado, Laurent Chabaud, Mathieu Pucheault and Jean-François Paquin
Beilstein J. Org. Chem. 2020, 16, 3069–3077. https://doi.org/10.3762/bjoc.16.256

How to Cite

Gilbert, A.; Langowski, P.; Delgado, M.; Chabaud, L.; Pucheault, M.; Paquin, J.-F. Beilstein J. Org. Chem. 2020, 16, 3069–3077. doi:10.3762/bjoc.16.256

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 7.7 MB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Nguyen, T. M.; Popek, L.; Matchavariani, D.; Blanchard, N.; Bizet, V.; Cahard, D. Expanding Radical Chloropentafluorosulfanylation of Alkynes. Organic letters 2024, 26, 365–369. doi:10.1021/acs.orglett.3c04043
  • Yasuo, E.; Aikawa, K.; Nozaki, K.; Okazoe, T. Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ6-sulfanes to tetrafluoroethylene. Chemical science 2023, 14, 12379–12385. doi:10.1039/d3sc04837c
  • Nguyen, T. M.; Legault, C. Y.; Blanchard, N.; Bizet, V.; Cahard, D. Tracking SF5 I in the Iodopentafluorosulfanylation of Alkynes. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202302914. doi:10.1002/chem.202302914
  • Mastalerz, V.; Lam, K.; Paquin, J.-F. Exploration toward the synthesis of aliphatic SF5-containing compounds using the Kolbe reaction. Journal of Fluorine Chemistry 2023, 268, 110113. doi:10.1016/j.jfluchem.2023.110113
  • Ouellet-Du Berger, M.-R.; Boucher, M.; Paquin, J.-F. Light-activation of SF5Cl for the atom transfer radical addition onto alkenes and alkynes. Journal of Fluorine Chemistry 2023, 268, 110131. doi:10.1016/j.jfluchem.2023.110131
  • Popek, L.; Cabrera‐Trujillo, J. J.; Debrauwer, V.; Blanchard, N.; Miqueu, K.; Bizet, V. Regio‐ and Stereoselective Hydroelementation of SF5‐Alkynes and Further Functionalizations. Angewandte Chemie 2023, 135. doi:10.1002/ange.202300685
  • Popek, L.; Cabrera-Trujillo, J. J.; Debrauwer, V.; Blanchard, N.; Miqueu, K.; Bizet, V. Regio- and Stereoselective Hydroelementation of SF5 -Alkynes and Further Functionalizations. Angewandte Chemie (International ed. in English) 2023, 62, e202300685. doi:10.1002/anie.202300685
  • Turani‐I‐Belloto, K.; Valero‐Pedraza, M.; Petit, E.; Chiriac, R.; Toche, F.; Granier, D.; Yot, P. G.; Alauzun, J. G.; Demirci, U. B. Solid‐State Structures of Primary Long‐Chain Alkylamine Borane Adducts – Synthesis, Properties and Computational Analysis. ChemistrySelect 2022, 7. doi:10.1002/slct.202203533
  • 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
  • Taponard, A.; Jarrosson, T.; Khrouz, L.; Médebielle, M.; Broggi, J.; Tlili, A. Metal‐Free SF6Activation: A New SF5‐Based Reagent Enables Deoxyfluorination and Pentafluorosulfanylation Reactions. Angewandte Chemie 2022, 134. doi:10.1002/ange.202204623
  • Taponard, A.; Jarrosson, T.; Khrouz, L.; Médebielle, M.; Broggi, J.; Tlili, A. Metal-Free SF6 Activation: A New SF5 -Based Reagent Enables Deoxyfluorination and Pentafluorosulfanylation Reactions. Angewandte Chemie (International ed. in English) 2022, 61, e202204623. doi:10.1002/anie.202204623
  • Sani, M.; Zanda, M. Recent Advances in the Synthesis and Medicinal Chemistry of SF5 and SF4Cl Compounds. Synthesis 2022, 54, 4184–4209. doi:10.1055/a-1845-9291
  • Haufe, G. Synthesis and application of pentafluorosulfanylation reagents and derived aliphatic SF5-containing building blocks. Tetrahedron 2022, 109, 132656. doi:10.1016/j.tet.2022.132656
  • Jose, A.; Guest, D.; LeGay, R.; Tizzard, G. J.; Coles, S. J.; Derveni, M.; Wright, E.; Marrison, L.; Lee, A. A.; Morris, A.; Robinson, M.; von Delft, F.; Fearon, D.; Koekemoer, L.; Matviuk, T.; Aimon, A.; Schofield, C. J.; Malla, T. R.; London, N.; Greenland, B. W.; Bagley, M. C.; Spencer, J.; The Covid Moonshot Consortium. Expanding the Repertoire of Low-Molecular-Weight Pentafluorosulfanyl-Substituted Scaffolds. ChemMedChem 2022, 17, e202100641. doi:10.1002/cmdc.202100641
  • Birepinte, M.; Champagne, P. A.; Paquin, J.-F. Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes. Angewandte Chemie (International ed. in English) 2021, 61, e202112575. doi:10.1002/anie.202112575
  • Birepinte, M.; Champagne, P. A.; Paquin, J. Photoinitiated anti‐Hydropentafluorosulfanylation of Terminal Alkynes. Angewandte Chemie 2021, 134. doi:10.1002/ange.202112575
  • Feng, F.-F.; Ma, J.-A.; Cahard, D. Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF 5 Ketones. The Journal of organic chemistry 2021, 86, 13808–13816. doi:10.1021/acs.joc.1c01886
  • Dudziński, P.; Husstedt, W. S.; Matsnev, A. V.; Thrasher, J. S.; Haufe, G. Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues. Organic & biomolecular chemistry 2021, 19, 5607–5623. doi:10.1039/d1ob00870f
  • Shou, J.; Xu, X.; Qing, F. Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride. Angewandte Chemie 2021, 133, 15399–15403. doi:10.1002/ange.202103606
  • Shou, J.-Y.; Xu, X.-H.; Qing, F.-L. Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride. Angewandte Chemie (International ed. in English) 2021, 60, 15271–15275. doi:10.1002/anie.202103606
Other Beilstein-Institut Open Science Activities