20372-72-9Relevant articles and documents
Visible light-promoted metal-free C-H activation: Diarylketone-catalyzed selective benzylic mono- and difluorination
Xia, Ji-Bao,Zhu, Chen,Chen, Chuo
supporting information, p. 17494 - 17500 (2014/01/06)
We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.
Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
Yoshino, Hideaki,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko,Oshima, Koichiro,Matsubara, Seijiro
, p. 29 - 35 (2007/10/03)
Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling them and the possibility of non-aqueous work-up. An ionic liquid, 3-ethyl-1-methyimidazolium oligo hydrogen fluoride (EMIMF(HF)2.3), which is stable in air and moisture, can be used as a hydrogen fluoride equivalent for some fluorination reactions; it does not require an aqueous work-up.
TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE: AN EFFECTIVE SOURCE OF FLUORIDE ION FOR HALOFLUORINATION OF ALKENES
Albanese, Domenico,Landini, Dario,Penso, Michele,Pratelli, Marco
, p. 537 - 541 (2007/10/02)
Vicinal halofluorides have been prepared from the corresponding alkenes by reaction with a stoichiometric amount of Bu4N+H2F3- as a source of fluoride anion and an excess of an N-halosuccinimide (NXS).The reaction products are obtained in good yields, with a prevalent Markownikoff regiochemistry.Olefins containing hydroxy, epoxy, acetoxy and alkoxy groups do not undergo side reactions under these reaction conditions.