133512-60-4Relevant academic research and scientific papers
Pentafluoroethylation of Arenediazonium Tetrafluoroborates Using On-Site Generated Tetrafluoroethylene
Xing, Bo,Li, Lingchun,Ni, Chuanfa,Hu, Jinbo
, p. 1131 - 1136 (2019/10/22)
Copper-mediated pentafluoroethylation of arenediazonium tetrafluoroborates with tetrafluoroethylene (TFE) on-site generated from TMSCF3 has been developed as a new method to prepare pentafluoroethyl arenes. The active pentafluoroethylation reagent “CuC2F5” is pre-generated from CuSCN, TFE and CsF, and its generation and further reaction are strongly solvent-dependent. This pentafluoroethylation reaction represents the first example of Sandmeyer-type pentafluoroethylation, which exhibits good functional group tolerance and potential applications for the synthesis of complicated bioactive compounds.
From C1 to C2: TMSCF3 as a Precursor for Pentafluoroethylation
Xie, Qiqiang,Li, Lingchun,Zhu, Ziyue,Zhang, Rongyi,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 13211 - 13215 (2018/09/25)
A highly efficient copper-mediated aromatic pentafluoroethylation method using TMSCF3 as the sole fluoroalkyl source is described. The reaction proceeds by a key C1 to C2 process, that is, the generation of CuCF3 from TMSCF3, followed by a subsequent spontaneous transformation into CuC2F5. Various aryl iodides were pentafluoroethylated with the TMSCF3-derived CuC2F5. This method represents the first practical and efficient method for pentafluoroethylation of aryl iodides using commercially available TMSCF3 as a pentafluoroethyl precursor.
CuI-Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl CuI Intermediate
Ohashi, Masato,Ishida, Naoyoshi,Ando, Kota,Hashimoto, Yu,Shigaki, Anna,Kikushima, Kotaro,Ogoshi, Sensuke
supporting information, p. 9794 - 9798 (2018/07/25)
The Cu(I)-catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC2F5, was isolated and its molecular structure confirmed by a single-crystal X-ray diffraction analysis. The key to the successful suppression of the competing oligomerization of TFE is to refrain from stirring the reaction mixture. A mechanistic study clearly discarded the possibility that the catalytic reaction proceeds via a radical pathway.
Stoichiometric and Catalytic Aryl-Perfluoroalkyl Coupling at Tri-tert-butylphosphine Palladium(II) Complexes
Ferguson, Devin M.,Bour, James R.,Canty, Allan J.,Kampf, Jeff W.,Sanford, Melanie S.
supporting information, p. 11662 - 11665 (2017/09/07)
This Communication describes studies of Ph-RF (RF = CF3 or CF2CF3) coupling at Pd complexes of general structure (PtBu3)PdII(Ph)(RF). The CF3 analogue participates in fast Ph-CF3 coupling (II complex. Furthermore, they show that this undesired pathway can be circumvented by changing from a CF3 to a CF2CF3 ligand. Ultimately, the insights gained from stoichiometric studies enabled the identification of Pd(PtBu3)2 as a catalyst for the Pd-catalyzed cross-coupling of aryl bromides with TMSCF2CF3 to afford pentafluoroethylated arenes.
Pentafluoroethylbenziodoxole (BIX-C2F5): A Shelf-Stable Reagent for Pentafluoroethylation of β-Ketoesters and Arylboronic Acids
Zhu, Jiansheng,Li, Yuguang,Ni, Chuanfa,Shen, Qilong
, p. 662 - 668 (2016/07/22)
An improved method for the preparation of pentafluoroethylating reagent pentafluoroethyl-substituted benziodoxole (BIX-C2F5) was described. Under mild conditions, BIX-C2F5was able to react with β-ketoesters or aryl/heteroaryl boronic acids to generate pentafluoroethylated compounds in good yields.
PENTAFLUOROETHYLATING COMPOSITIONS
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Page/Page column 37; 38, (2015/02/25)
The present invention relates to pentafluoroethylating compositions, processes for obtaining them, and their use in pentafluoroethylation reactions.
Pentafluoroethylating compositions
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Paragraph 0194, (2015/02/25)
The present invention relates to pentafluoroethylating compositions, processes for obtaining them, and their use in pentafluoroethylation reactions.
Cupration of C2F5H: Isolation, structure, and synthetic applications of [K(DMF)2][(t -BuO)Cu(C2F 5)]. Highly efficient pentafluoroethylation of unactivated aryl bromides
Lishchynskyi, Anton,Grushin, Vladimir V.
supporting information, p. 12584 - 12587 (2013/09/23)
Pentafluoroethane, C2F5H (HFC-125), is smoothly cuprated with preisolated or in situ-generated [K(DMF)][(t-BuO)2Cu] to give [K(DMF)2][(t-BuO)Cu(C2F5)] (1) in nearly quantitative yield. Complex 1 has been isolated, structurally characterized, and demonstrated to be an exceedingly versatile pentafluoroethylating reagent for a variety of substrates, including unactivated aryl bromides.
A NOVEL AND CONVENIENT METHOD FOR TRIFLUOROMETHYLATION OF ORGANIC HALIDES USING CF3SiR'3/KF/Cu(I) SYSTEM
Urata, Hisao,Fuchikami, Takamasa
, p. 91 - 94 (2007/10/02)
Fluoride ion induced cross-coupling reaction of organic halides with trifluoromethyltrialkylsilanes takes place in the presence of Cu(I) salts under mild reaction conditions to give the corresponding trifluoromethylated products in high yields.
