CuI -Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl CuI Intermediate

Chemistry : a European Journal
Masato OhashiSensuke Ogoshi

Abstract

The Cu(I)-catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC2 F5 , 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.

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Citations

Dec 19, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Otohiro GotsuToshio Kubota
May 24, 2019·Angewandte Chemie·Jia-Xiang XiangFeng-Ling Qing
Jan 7, 2021·Organic & Biomolecular Chemistry·Dayanne R Carvalho, Alec H Christian
May 29, 2020·Organic Letters·Xinkan Yang, Gavin Chit Tsui
Jul 16, 2019·Journal of the American Chemical Society·Nicholas O AndrellaR Tom Baker
Jul 17, 2019·The Journal of Organic Chemistry·Fazhi YuYonghui Wang
Dec 4, 2021·Journal of the American Chemical Society·Kenta MoriTakashi Okazoe

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