Supporting Information
Supporting Information File 1: Experimental details and copies of 1H-, 19F-, and 13C NMR spectra of new products. | ||
Format: PDF | Size: 7.8 MB | Download |
Cite the Following Article
Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of “super-trifluoromethyl” arene chemistry and its industry
Teruo Umemoto, Lloyd M. Garrick and Norimichi Saito
Beilstein J. Org. Chem. 2012, 8, 461–471.
https://doi.org/10.3762/bjoc.8.53
How to Cite
Umemoto, T.; Garrick, L. M.; Saito, N. Beilstein J. Org. Chem. 2012, 8, 461–471. doi:10.3762/bjoc.8.53
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.
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Bonetti, K. A.; Rende, D.; Murphy, M.; Welch, J. T. Photocurable Hypervalent Fluorinated Sulfur Containing Thin Films with Remarkable Hardness and Modulus. Molecules (Basel, Switzerland) 2024, 29, 4413. doi:10.3390/molecules29184413
- Bizet, V.; Abd El Sater, M.; Popek, L.; Blanchard, N. Recent Advances in the Chemistry and Application of SF5-Compounds. Synthesis 2024. doi:10.1055/a-2383-6620
- Kucher, H.; Wenzel, J. O.; Rombach, D. Hydrothiolation of Triisopropylsilyl Acetylene Sulfur Pentafluoride - Charting the Chemical Space of β-SF5 Vinyl Sulfides. ChemPlusChem 2024, 89, e202400168. doi:10.1002/cplu.202400168
- Kraemer, Y.; Buldt, J. A.; Kong, W.-Y.; Stephens, A. M.; Ragan, A. N.; Park, S.; Haidar, Z. C.; Patel, A. H.; Shey, R.; Dagan, R.; McLoughlin, C. P.; Fettinger, J. C.; Tantillo, D. J.; Pitts, C. R. Overcoming a Radical Polarity Mismatch in Strain-Release Pentafluorosulfanylation of [1.1.0]Bicyclobutanes: An Entryway to Sulfone- and Carbonyl-Containing SF5-Cyclobutanes. Angewandte Chemie (International ed. in English) 2024, 63, e202319930. doi:10.1002/anie.202319930
- Kraemer, Y.; Buldt, J. A.; Kong, W.; Stephens, A. M.; Ragan, A. N.; Park, S.; Haidar, Z. C.; Patel, A. H.; Shey, R.; Dagan, R.; McLoughlin, C. P.; Fettinger, J. C.; Tantillo, D. J.; Pitts, C. R. Overcoming a Radical Polarity Mismatch in Strain‐Release Pentafluorosulfanylation of [1.1.0]Bicyclobutanes: An Entryway to Sulfone‐ and Carbonyl‐Containing SF5‐Cyclobutanes. Angewandte Chemie 2024, 136. doi:10.1002/ange.202319930
- 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
- Ritchhart, A.; Chen, Z.; Behera, A.; Jeon, I.-R.; Chapman, K. W.; Vaikuntanathan, S.; Anderson, J. S. Cluster-Spin-Glass Magnetic Behavior and Morphology in the Coordination Polymer Alloys FeyCo1-yBTT. Journal of the American Chemical Society 2023, 145, 24089–24097. doi:10.1021/jacs.3c07527
- Nikul'shin, P. V.; Maksimov, A. M.; Gatilov, Y. V.; Kovtonyuk, V. N.; Bredikhin, R. A. One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid. Mendeleev Communications 2023, 33, 721–722. doi:10.1016/j.mencom.2023.09.041
- Aggarwal, T.; Hada, K.; Murata, Y.; Sumii, Y.; Tanagawa, K.; Niina, K.; Mori, S.; Escorihuela, J.; Shibata, N. Regio- and Z-Selective Alkyne Hydroamination and Hydrophenoxylation using Tetrafluoro-λ6 -Sulfanyl Alkynes under Superbasic, Naked Anion Conditions. Angewandte Chemie (International ed. in English) 2023, 62, e202307090. doi:10.1002/anie.202307090
- Aggarwal, T.; Hada, K.; Murata, Y.; Sumii, Y.; Tanagawa, K.; Niina, K.; Mori, S.; Escorihuela, J.; Shibata, N. Regio‐ and Z‐Selective Alkyne Hydroamination and Hydrophenoxylation using Tetrafluoro‐λ6‐Sulfanyl Alkynes under Superbasic, Naked Anion Conditions. Angewandte Chemie 2023, 135. doi:10.1002/ange.202307090
- Kordnezhadian, R.; Zogu, A.; Borgarelli, C.; Van Lommel, R.; Demaerel, J.; De Borggraeve, W. M.; Ismalaj, E. De-Risking S-F Bond Formation: A Gas Cylinder-Free Strategy to Access S(IV) and S(VI) Fluorinated Compounds. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202300361. doi:10.1002/chem.202300361
- Mori, S.; Hada, K.; Shibata, N. 直線的分子連結を実現するテトラフルオロスルファニル化合物群:合成と開拓. Journal of Synthetic Organic Chemistry, Japan 2023, 81, 428–438. doi:10.5059/yukigoseikyokaishi.81.428
- Mori, S.; Kagechika, H. Development of Bioactive Molecules Bearing Hexacoordinated Sulfur Fluoride. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 2023, 143, 429–434. doi:10.1248/yakushi.22-00205-2
- James, R. D.; Alqahtani, L. S.; Mallows, J.; Flint, H. V.; Waddell, P. G.; Woodford, O. J.; Gibson, E. A. Pentafluorosulfanyl-functionalised BODIPY push-pull dyes for p-type dye-sensitized solar cells. Sustainable energy & fuels 2023, 7, 1494–1501. doi:10.1039/d2se00977c
- Mahmoud, E. M.; Iwasaki, H.; Hada, K.; Murata, Y.; Sumii, Y.; Shibata, N. Synthesis of Pyridine-SF4-Alkynes via Light-Promoted Radical Coupling of Pyridine-SF4-Chlorides and EBX Reagents. Bulletin of the Chemical Society of Japan 2022, 96, 110–112. doi:10.1246/bcsj.20220330
- Dudziński, P.; Matsnev, A. V.; Thrasher, J. S.; Haufe, G. Reactions of difluoro-pentafluorosulfanyl-iodomethane (SF5CF2I) with electronically different types of alkenes. Journal of Fluorine Chemistry 2022, 264, 110051. doi:10.1016/j.jfluchem.2022.110051
- Zhao, X.; Shou, J.-Y.; Newton, J. J.; Qing, F.-L. trans-Trifluoromethyltetrafluorosulfanyl Chloride: Selective Synthesis and Reaction with Diazo Compounds. Organic letters 2022, 24, 8412–8416. doi:10.1021/acs.orglett.2c03540
- Eder, T.; Buß, F.; Wilm, L. F. B.; Seidl, M.; Podewitz, M.; Dielmann, F. Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF5−Salt Accessible from SF6. Angewandte Chemie 2022, 134. doi:10.1002/ange.202209067
- Eder, T.; Buß, F.; Wilm, L. F. B.; Seidl, M.; Podewitz, M.; Dielmann, F. Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF5 - Salt Accessible from SF6. Angewandte Chemie (International ed. in English) 2022, 61, e202209067. doi:10.1002/anie.202209067
- Mori, S.; Tsuemoto, N.; Kawachi, E.; Takubo, C.; Tanatani, A.; Kagechika, H. Development of retinoic acid receptor antagonists bearing trans-SF4-alkynyl structure as a linear linker. Tetrahedron 2022, 123, 132967. doi:10.1016/j.tet.2022.132967
Patents
- GENIN SCOTT NICHOLAS; HELANDER MICHAEL. Materials for forming a nucleation-inhibiting coating and devices incorporating same. US 12101987 B2, Sept 24, 2024.
- CHANG YI-LU; WANG QI; GAO DONG; GENIN SCOTT NICHOLAS; HELANDER MICHAEL; QIU JACKY; WANG ZHIBIN. Method for patterning a coating on a surface and device including a patterned coating. US 12069939 B2, Aug 20, 2024.
- HELANDER MICHAEL; GENIN SCOTT NICHOLAS. Materials for forming a nucleation-inhibiting coating and devices incorporating same. US 12069938 B2, Aug 20, 2024.
- HELANDER MICHAEL; WANG ZHIBIN. Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating. US 11985841 B2, May 14, 2024.
- CHANG YI-LU; WANG QI; GENIN SCOTT NICHOLAS; HELANDER MICHAEL; QIU JACKY; WANG ZHIBIN; LESSARD BENOIT. Materials for forming a nucleation-inhibiting coating and devices incorporating same. US 11751415 B2, Sept 5, 2023.
- HELANDER MICHAEL; GENIN SCOTT NICHOLAS; WANG ZHIBIN. Materials for forming a nucleation-inhibiting coating and devices incorporating same. US 11730012 B2, Aug 15, 2023.
- CHANG YI-LU; WANG QI; GAO DONG; GENIN SCOTT NICHOLAS; HELANDER MICHAEL; QIU JACKY; WANG ZHIBIN. Patterned conductive coating for surface of an opto-electronic device. US 11581487 B2, Feb 14, 2023.
- OKAZOE TAKASHI; GATZENMEIER TIM; NOZAKI KYOKO. METHOD FOR PRODUCING PENTAFLUOROSULFANYL GROUP-CONTAINING ARYL COMPOUND. WO 2022186304 A1, Sept 9, 2022.
- SHIBATA NORIO; SAITO NORIMICHI. Method of producing pentafluorosulfanyl aromatic compound. US 11014887 B2, May 25, 2021.
- SHIBATA NORIO; MATSUZAKI KOHEI; SAITO NORIMICHI. PENTAFLUOROSULFANYLPYRIDYL-GROUP-CONTAINING DIARYLIODONIUM SALT. WO 2017090305 A1, June 1, 2017.
- WELCH JOHN; ZHONG LINBIN. Aryl tetrafluorosulfanyl compounds. US 9174934 B2, Nov 3, 2015.
- RÖSCHENTHALER GERD-VOLKER; BEIER PETR; LUMMER KATRIN; PONOMARENKO MAXIM. VERFAHREN ZUR HERSTELLUNG VON ARYLSCHWEFELPENTAFLUORIDEN. DE 102013104346 A1, Oct 30, 2014.