Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide

Yuzo Nakamura, Motohiro Fujiu, Tatsuya Murase, Yoshimitsu Itoh, Hiroki Serizawa, Kohsuke Aikawa and Koichi Mikami
Beilstein J. Org. Chem. 2013, 9, 2404–2409. https://doi.org/10.3762/bjoc.9.277

Cite the Following Article

Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
Yuzo Nakamura, Motohiro Fujiu, Tatsuya Murase, Yoshimitsu Itoh, Hiroki Serizawa, Kohsuke Aikawa and Koichi Mikami
Beilstein J. Org. Chem. 2013, 9, 2404–2409. https://doi.org/10.3762/bjoc.9.277

How to Cite

Nakamura, Y.; Fujiu, M.; Murase, T.; Itoh, Y.; Serizawa, H.; Aikawa, K.; Mikami, K. Beilstein J. Org. Chem. 2013, 9, 2404–2409. doi:10.3762/bjoc.9.277

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

  • Gladkov, A. A.; Levin, V. V.; Dilman, A. D. Photoredox Activation of Fluorinated Organozinc Reagents: Hydrofluoroalkylation of Unactivated and Electron Deficient Alkenes. The Journal of organic chemistry 2024, 89, 11826–11835. doi:10.1021/acs.joc.4c01623
  • Morisaki, K.; Miyamoto, K.; Kawaguchi, E.; Sato, Y. Zn/F carbenoids: preparation, structures, stability, and application to nucleophilic monofluoroalkylation. Organic Chemistry Frontiers 2024, 11, 4194–4206. doi:10.1039/d4qo00648h
  • Hong, B.; Teng, Y.; Fang, Z.; Wu, W.; Weng, Z. Synthesis of 2‐Trifluoromethyl Pyridines through Multicomponent Kröhnke Reaction. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202400299
  • Segovia, C. M.; Porto, L. L. T. N.; Casasús, P.; Bascuas, I.; Ahmad, A.; Mestre, J.; Bernús, M.; Castillón, S.; Baker, R. T.; Boutureira, O. Tetrafluoroethylation of Electron‐Rich Alkenyl Iodides Enabled by in situ Generation of Solvent‐Stabilized "Ligandless" CuCF2CF2H. Advanced Synthesis & Catalysis 2024, 366, 2684–2690. doi:10.1002/adsc.202301409
  • Dinh, H. M.; He, Y.; Fayzullin, R. R.; Vasylevskyi, S.; Khaskin, E.; Khusnutdinova, J. R. Synthesis of Aryl‐Manganese(III) Fluoride Complexes via α‐Fluorine Elimination from CF3 and Difluorocarbene Generation. European Journal of Inorganic Chemistry 2023, 26. doi:10.1002/ejic.202300460
  • Wang, Q.; Hu, J. doi:10.1002/9783527830237.ch15
  • Lalloo, N.; Malapit, C. A.; Taimoory, S. M.; Brigham, C. E.; Sanford, M. S. Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis. Journal of the American Chemical Society 2021, 143, 18617–18625. doi:10.1021/jacs.1c08551
  • Adekenova, K. S.; Wyatt, P. B.; Adekenov, S. M. The preparation and properties of 1,1-difluorocyclopropane derivatives. Beilstein journal of organic chemistry 2021, 17, 245–272. doi:10.3762/bjoc.17.25
  • Uchikura, T.; Kamiyama, N.; Ishikawa, T.; Akiyama, T. Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent. Beilstein journal of organic chemistry 2020, 16, 2442–2447. doi:10.3762/bjoc.16.198
  • Panja, C.; Puttaramu, J. V.; Chandran, T. K.; Nimje, R. Y.; Kumar, H.; Gupta, A.; Arunachalam, P. N.; Corte, J. R.; Mathur, A. Methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA)/copper (I) iodide mediated and tetrabutylammonium iodide promoted trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles. Journal of Fluorine Chemistry 2020, 236, 109516. doi:10.1016/j.jfluchem.2020.109516
  • Bischoff, L. A.; Riefer, J.; Wirthensohn, R.; Bischof, T.; Bertermann, R.; Ignat'ev, N. V.; Finze, M. Pentafluoroethylaluminates: A Combined Synthetic, Spectroscopic, and Structural Study. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 13615–13620. doi:10.1002/chem.202000667
  • Ergun, S.; Casselman, M. D.; Kaur, A. P.; Attanayake, N. H.; Parkin, S.; Odom, S. A. Improved synthesis of N-ethyl-3,7-bis(trifluoromethyl)phenothiazine. New Journal of Chemistry 2020, 44, 11349–11355. doi:10.1039/d0nj00184h
  • Kalkman, E. D.; Mormino, M. G.; Hartwig, J. F. Unusual Electronic Effects of Ancillary Ligands on the Perfluoroalkylation of Aryl Iodides and Bromides Mediated by Copper(I) Pentafluoroethyl Complexes of Substituted Bipyridines. Journal of the American Chemical Society 2019, 141, 19458–19465. doi:10.1021/jacs.9b10540
  • Mestre, J.; Castillón, S.; Boutureira, O. “Ligandless” Pentafluoroethylation of Unactivated (Hetero)aryl and Alkenyl Halides Enabled by the Controlled Self-Condensation of TMSCF3-Derived CuCF3. The Journal of organic chemistry 2019, 84, 15087–15097. doi:10.1021/acs.joc.9b02001
  • Kawamura, S.; Sodeoka, M. Fluoroalkylation Methods for Synthesizing Versatile Building Blocks. Bulletin of the Chemical Society of Japan 2019, 92, 1245–1262. doi:10.1246/bcsj.20190080
  • Liu, Z.; Shen, H.; Xiao, H.; Wang, Z.; Zhu, L.; Li, C. Copper-Catalyzed Ring-Opening Radical Trifluoromethylation of Cycloalkanone Oximes. Organic letters 2019, 21, 5201–5205. doi:10.1021/acs.orglett.9b01803
  • Ono, S.; Yokota, Y.; Ito, S.; Mikami, K. Regiocontrolled Heptafluoroisopropylation of Aromatic Halides by Copper(I) Carboxylates with Heptafluoroisopropyl-Zinc Reagents. Organic letters 2019, 21, 1093–1097. doi:10.1021/acs.orglett.8b04147
  • Ferguson, D. M.; Bour, J. R.; Canty, A. J.; Kampf, J. W.; Sanford, M. S. Aryl–CF3 Coupling from Phosphinoferrocene-Ligated Palladium(II) Complexes. Organometallics 2019, 38, 519–526. doi:10.1021/acs.organomet.8b00828
  • Haupt, A.; Lentz, D. Corannulenes with Electron-Withdrawing Substituents: Synthetic Approaches and Resulting Structural and Electronic Properties. Chemistry (Weinheim an der Bergstrasse, Germany) 2018, 25, 3440–3454. doi:10.1002/chem.201803927
  • Xie, Q.; Li, L.; Zhu, Z.; Zhang, R.; Ni, C.; Hu, J. From C 1 to C 2 : TMSCF 3 as a Precursor for Pentafluoroethylation. Angewandte Chemie (International ed. in English) 2018, 57, 13211–13215. doi:10.1002/anie.201807873
Other Beilstein-Institut Open Science Activities