1417820-87-1Relevant articles and documents
Synergistic lewis acid and photoredox-catalyzed trifluoromethylative difunctionalization of alkenes with selenium ylide-based trifluoromethylating reagent
Shen, Qilong,Ge, Hangming,Wu, Botao,Liu, Yafei,Wang, Haoyang
, p. 12414 - 12424 (2020/11/10)
Trifluoromethylative difunctionalization of alkenes with a variety of nucleophiles including amine, azide, alcohol, water, and electron-rich arenes using reagent 1 as trifluoromethyl radical source in the presence of a synergistic catalyst including a Lewis acid scandium(III) trifluoromethanesulfonate (Sc(OTf)3) and a photoredox catalyst [fac-Ir(ppy)3] was described. Mechanistic studies showed that the role of Sc(OTf)3 in the reaction is to activate reagent 1 via Lewis acid?Lewis base interaction to form complex [Sc(OTf)3?3(1)], which was fully characterized by nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and elemental analysis. Cyclic voltammetry (CV) experiments and density functional theory (DFT) calculation showed that the reduction potential of complex [Sc(OTf)3?3(1)] is much higher than that of reagent 1, thus suggesting complex [Sc(OTf)3?3(1)] is much easier to accept electron through single-electron-transfer (SET) process, and consequently, much easier to generate trifluoromethyl radical.
Method for preparing hydroxyl and trifluoromethyl substituted compounds through reaction of olefin and trifluo-romethyl bromide
-
Paragraph 0050-0058; 0197-0204, (2020/01/14)
The invention discloses a method for preparing hydroxyl and trifluoromethyl substituted compounds through olefin addition reaction. According to the method, a compound containing carbon-carbon doublebonds and trifluo-romethyl bromide are taken as raw materials, a metal salt-tertiary amine system is taken as a catalyst, air is taken as an oxidizing agent, carbon-carbon double bonds can be subjected to addition reaction, and compounds with hydroxyl substitution and trifluoromethyl substitution at the same time are prepared; wherein the metal salt is one or more selected from a cobalt salt, a silver salt, a bismuth salt, a nickel salt, an iron salt or a copper salt; the tertiary amine is N-isopropyl-N-methyl-tert-butylamine or N, N-diisopropylethylamine. According to the method, the metal salt-tertiary amine system is taken as a catalyst for the first time, hydroxyl substitution and trifluoromethyl substitution of olefins are realized, one-step reaction is enough, reaction process conditions are mild, reaction raw materials are cheap and easily available, cost is low, reaction substrates have strong applicability, and can participate in the reaction as long as carbon-carbon double bonds exist in the structures, and are not influenced by substituent groups on double bond carbon atoms, and the product yield is high.
