60979-15-9Relevant academic research and scientific papers
Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF3
Pan, Shitao,Xie, Qiqiang,Wang, Xiu,Wang, Qian,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 5156 - 5159 (2022/04/21)
The TMSCF3-derived CuCF2CF3 species has been successfully applied in pentafluoroethylation of organoboronates and terminal alkynes. By using 1,10-phenanthroline as a ligand, a broad range of (hetero)arylboronates and alkenylboronates were smoothly pentafluoroethylated under aerobic conditions. Furthermore, terminal alkynes can undergo aerobic cross-coupling with the TMSCF3-derived CuCF2CF3 species in the absence of additional ligands.
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.
TMSCF3 as a Convenient Source of CF2=CF2 for Pentafluoroethylation, (Aryloxy)tetrafluoroethylation, and Tetrafluoroethylation
Li, Lingchun,Ni, Chuanfa,Xie, Qiqiang,Hu, Mingyou,Wang, Fei,Hu, Jinbo
supporting information, p. 9971 - 9975 (2017/08/08)
A new method for the on-site preparation of tetrafluoroethylene (TFE) and a procedure for its efficient use in pentafluoroethylation by fluoride addition were developed by using a simple two-chamber system. The on-site preparation of TFE was accomplished by dimerization of difluorocarbene derived from (trifluoromethyl)trimethylsilane (TMSCF3) under mild conditions. Other fluoroalkylation reactions, such as (aryloxy)tetrafluoroethylation and tetrafluoroethylation processes, were also achieved using a similar approach. This work not only demonstrates a convenient and safe approach for the generation and use of TFE in academic laboratories, but also provides a new strategy for pentafluoroethylation.
