Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

Takeshi Fujita, Ryo Kinoshita, Tsuyoshi Takanohashi, Naoto Suzuki and Junji Ichikawa
Beilstein J. Org. Chem. 2017, 13, 2682–2689. https://doi.org/10.3762/bjoc.13.266

Supporting Information

Supporting Information File 1: Detailed experimental procedures and spectral data.
Format: PDF Size: 5.3 MB Download

Cite the Following Article

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes
Takeshi Fujita, Ryo Kinoshita, Tsuyoshi Takanohashi, Naoto Suzuki and Junji Ichikawa
Beilstein J. Org. Chem. 2017, 13, 2682–2689. https://doi.org/10.3762/bjoc.13.266

How to Cite

Fujita, T.; Kinoshita, R.; Takanohashi, T.; Suzuki, N.; Ichikawa, J. Beilstein J. Org. Chem. 2017, 13, 2682–2689. doi:10.3762/bjoc.13.266

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: 130.8 KB Download

Citations to This Article

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

Scholarly Works

  • Feng, S.; Zhang, H.; Liu, J.; Shi, D.; Yang, W.; Zhu, H.; Zhang, X.; Fu, Z. Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides. The Journal of organic chemistry 2024, 89, 14537–14542. doi:10.1021/acs.joc.4c01587
  • Fuchibe, K.; Fujita, T.; Ichikawa, J. Pinpoint-fluorinated polycyclic aromatic hydrocarbons (F-PAHs) and their heteroaromatic analogs: syntheses, reactivities, and properties. Bulletin of the Chemical Society of Japan 2023, 97. doi:10.1093/bulcsj/uoad024
  • Lou, Z.; Hu, J.; Ni, C.; Wang, X.; Hu, J. Unusual Single Electron Transfer Reactions between Alkenes and Iodine Electrophiles†. Chinese Journal of Chemistry 2023, 42, 471–477. doi:10.1002/cjoc.202300611
  • Sun, G.; Liu, H.; Wang, X.; Zhang, W.; Miao, W.; Luo, Q.; Gao, B.; Hu, J. Palladium‐Catalyzed Defluorinative Coupling of Difluoroalkenes and Aryl Boronic Acids for Ketone Synthesis. Angewandte Chemie 2022, 135. doi:10.1002/ange.202213646
  • Sun, G.; Liu, H.; Wang, X.; Zhang, W.; Miao, W.; Luo, Q.; Gao, B.; Hu, J. Palladium-Catalyzed Defluorinative Coupling of Difluoroalkenes and Aryl Boronic Acids for Ketone Synthesis. Angewandte Chemie (International ed. in English) 2022, 62, e202213646. doi:10.1002/anie.202213646
  • Miller, E.; Mai, B. K.; Read, J. A.; Bell, W. C.; Derrick, J. S.; Liu, P.; Toste, F. D. A Combined DFT, Energy Decomposition, and Data Analysis Approach to Investigate the Relationship Between Noncovalent Interactions and Selectivity in a Flexible DABCOnium/Chiral Anion Catalyst System. ACS catalysis 2022, 12, 12369–12385. doi:10.1021/acscatal.2c03077
  • Kong, T.; Hu, J. Difluoromethyl 2-Pyridyl Sulfone: A Versatile Reagent for the Synthesis of Organofluorine Compounds. Perfluoroalkyl Substances; The Royal Society of Chemistry, 2022; pp 113–145. doi:10.1039/9781839167591-00113
  • Lee, S.; Chung, W. Enantioselective halogenation via asymmetric phase‐transfer catalysis. Bulletin of the Korean Chemical Society 2022, 43, 896–911. doi:10.1002/bkcs.12546
  • Sorrentino, J. P.; Altman, R. A. Fluorine-Retentive Strategies for the Functionalization of gem-Difluoroalkenes. Synthesis 2021, 53, 3935–3950. doi:10.1055/a-1547-9270
  • Tiekink, E. R. T. Supramolecular architectures sustained by delocalised C–I⋯π(arene) interactions in molecular crystals and the propensity of their formation. CrystEngComm 2021, 23, 904–928. doi:10.1039/d0ce01677b
  • Jiang, Q.; Liang, Y.; Zhang, Y.; Zhao, X. Chalcogenide-Catalyzed Intermolecular Electrophilic Thio- and Halofunctionalization of gem-Difluoroalkenes: Construction of Diverse Difluoroalkyl Sulfides and Halides. Organic letters 2020, 22, 7581–7587. doi:10.1021/acs.orglett.0c02784
  • Miller, E. G.; Kim, S.; Gibson, K.; Derrick, J. S.; Toste, F. D. Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters. Journal of the American Chemical Society 2020, 142, 8946–8952. doi:10.1021/jacs.0c02331
  • Fedorov, O. V.; Scherbinina, S. I.; Levin, V. V.; Dilman, A. D. Light-Mediated Dual Phosphine-/Copper-Catalyzed Atom Transfer Radical Addition Reaction. The Journal of organic chemistry 2019, 84, 11068–11079. doi:10.1021/acs.joc.9b01649
  • Zhang, R.; Ni, C.; Zhao, Y.; Hu, J. Synthesis of 2,2-diaryl-1,1-difluoroethenes via Pd-catalyzed dehydrosulfonylative cross-coupling of α-[difluoro(phenylsulfonyl)methyl]benzyl tosylates with arylboronic acids. Tetrahedron 2018, 74, 5295–5302. doi:10.1016/j.tet.2018.04.054
Other Beilstein-Institut Open Science Activities