Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF3

Xueliang Jiang and Feng-Ling Qing
Beilstein J. Org. Chem. 2013, 9, 2862–2865.

Supporting Information

Supporting Information File 1: Experimental details, characterization data of all products and copies of NMR spectra.
Format: PDF Size: 1.8 MB Download

Cite the Following Article

Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF3
Xueliang Jiang and Feng-Ling Qing
Beilstein J. Org. Chem. 2013, 9, 2862–2865.

How to Cite

Jiang, X.; Qing, F.-L. Beilstein J. Org. Chem. 2013, 9, 2862–2865. doi:10.3762/bjoc.9.322

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

  • Shigeno, M.; Shishido, Y.; Soga, A.; Nozawa-Kumada, K.; Kondo, Y. Defluorinative Transformation of (2,2,2-Trifluoroethyl)arenes Catalyzed by the Phosphazene Base t-Bu-P2. The Journal of organic chemistry 2023, 88, 1796–1802. doi:10.1021/acs.joc.2c02034
  • Zhou, M.-X.; Han, S.; Wang, Y.; Zhang, W.; Wang, Z.; Zeng, Y.-F. Recent advances in trifluoroethylation reaction. Organic Chemistry Frontiers 2023. doi:10.1039/d3qo01366a
  • Zemtsov, A. A.; Levin, V. V.; Dilman, A. D. Allylic substitution reactions with fluorinated nucleophiles. Coordination Chemistry Reviews 2022, 459, 214455. doi:10.1016/j.ccr.2022.214455
  • Posevins, D.; Bermejo‐López, A.; Bäckvall, J. Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols. Angewandte Chemie 2021, 133, 22352–22357. doi:10.1002/ange.202106742
  • Posevins, D.; Bermejo-López, A.; Bäckvall, J.-E. Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols. Angewandte Chemie (International ed. in English) 2021, 60, 22178–22183. doi:10.1002/anie.202106742
  • Liu, Z.-Y.; Cook, S. P. Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates. Organic letters 2021, 23, 808–813. doi:10.1021/acs.orglett.0c04039
  • Li, H.; Sheng, J.; Liao, G.-X.; Wu, B.-B.; Ni, H.-Q.; Li, Y.; Wang, X.-S. Nickel-Catalyzed Direct Trifluoroethylation of Aryl Iodides with 1,1,1-Trifluoro-2-Iodoethane via Reductive Coupling. Advanced Synthesis & Catalysis 2020, 362, 5363–5367. doi:10.1002/adsc.202000985
  • Shutao, Q.; Shiquan, G.; Xie, X.; Yang, J.; Zhang, J. Palladium-Catalyzed Fluoroarylation of gem-Difluoroenynes to Access Trisubstituted Trifluoromethyl Allenes. Organic letters 2020, 22, 5229–5234. doi:10.1021/acs.orglett.0c01887
  • Nozawa-Kumada, K.; Osawa, S.; Ojima, T.; Noguchi, K.; Shigeno, M.; Kondo, Y. Transition‐Metal‐Free Trifluoromethylation of Benzyl Bromides Using Trifluoromethyltrimethylsilane and CsF in 1,2‐Dimethoxyethane. Asian Journal of Organic Chemistry 2020, 9, 765–768. doi:10.1002/ajoc.202000124
  • Zhao, Z.; Y., K. C.; Legault, C. Y.; Murphy, G. K. Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2‐Trifluoroethyl)arenes. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 11240–11245. doi:10.1002/chem.201902818
  • Chen, Y.; Ma, G.; Gong, H. Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni's Reagent. Organic letters 2018, 20, 4677–4680. doi:10.1021/acs.orglett.8b02005
  • Orsi, D. L.; Altman, R. A. Exploiting the unusual effects of fluorine in methodology. Chemical communications (Cambridge, England) 2017, 53, 7168–7181. doi:10.1039/c7cc02341c
  • Yang, S.-Y.; Han, W.; Zhang, D.-L.; Zhou, X.; Bai, M.; Cui, B.; Wan, N.-W.; Yuan, W.-C.; Chen, Y. Synthesis of Phenanthridines through Palladium‐Catalyzed Cascade Reaction of 2‐Halo‐N‐Ms‐arylamines with Benzyl Halides/Sulfonates. European Journal of Organic Chemistry 2017, 2017, 996–1003. doi:10.1002/ejoc.201601608
  • Kazakova, A. N.; Iakovenko, R. O.; Boyarskaya, I. A.; Ivanov, A. Y.; Avdontceva, M. S.; Zolotarev, A. A.; Panikorovsky, T. L.; Starova, G. L.; Nenajdenko, V. G.; Vasilyev, A. V. Brominated CF3-allyl alcohols as multicentered electrophiles in TfOH promoted reactions with arenes. Organic Chemistry Frontiers 2017, 4, 255–265. doi:10.1039/c6qo00643d
  • Beier, P.; Zibinsky, M.; Prakash, G. K. S. Organic Reactions - Nucleophilic Additions of Perfluoroalkyl Groups. Organic Reactions 2016, 1–492. doi:10.1002/0471264180.or091.01
  • Ambler, B. R.; Yang, M.-H.; Altman, R. A. Metal-catalyzed Decarboxylative Fluoroalkylation Reactions. Synlett : accounts and rapid communications in synthetic organic chemistry 2016, 27, 2747–2755. doi:10.1055/s-0036-1588637
  • Boreux, A.; Lonca, G. H.; Riant, O.; Gagosz, F. Synthesis of Trifluoromethyl-allenes by Gold-Catalyzed Rearrangement of Propargyl Benzyl Ethers. Organic letters 2016, 18, 5162–5165. doi:10.1021/acs.orglett.6b02636
  • Yang, J.; Han, Q.-Y.; Zhao, C.-L.; Dong, T.; Hou, Z.-Y.; Qin, H.-L.; Zhang, C.-P. Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl(2,2,2-trifluoroethyl)iodonium triflates. Organic & biomolecular chemistry 2016, 14, 7654–7658. doi:10.1039/c6ob01384h
  • Areephong, J.; Huo, B.; Mbaezue, I. I.; Ylijoki, K. E. O. Synthesis of dihydroquinoxaline-2(1H)-ones via palladium-catalyzed intramolecular C–N bond formation. Tetrahedron Letters 2016, 57, 3124–3126. doi:10.1016/j.tetlet.2016.06.008
  • Ji, Y.-L.; Luo, J.-J.; Lin, J.-H.; Xiao, J.-C.; Gu, Y.-C. Cu-Catalyzed C–H Trifluoromethylation of 3-Arylprop-1-ynes for the Selective Construction of Allenic Csp2–CF3 and Propargyl Csp3–CF3 Bonds. Organic letters 2016, 18, 1000–1003. doi:10.1021/acs.orglett.6b00120
Other Beilstein-Institut Open Science Activities