136476-18-1Relevant academic research and scientific papers
Flash generation and borylation of 1-(trifluoromethyl)vinyllithium toward synthesis of α-(trifluoromethyl)styrenes
Fujita, Takeshi,Konno, Naruki,Watabe, Yota,Ichitsuka, Tomohiro,Nagaki, Aiichiro,Yoshida, Jun-ichi,Ichikawa, Junji
, p. 72 - 76 (2018)
Thermally unstable (3,3,3-trifluoroprop-1-en-2-yl)lithium was generated by lithiation of 2-bromo-3,3,3-trifluoroprop-1-ene and successively underwent borylation in a flow microreactor system. Direct use of the 1-(trifluoromethyl)vinylborate thus formed for the Suzuki–Miyaura coupling in a batch system afforded α-(trifluoromethyl)styrenes in high yields.
A Chiral Pentafluorinated Isopropyl Group via Iodine(I)/(III) Catalysis
Meyer, Stephanie,H?fliger, Joel,Sch?fer, Michael,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
supporting information, p. 6430 - 6434 (2021/02/26)
An I(I)/(III) catalysis strategy to construct an enantioenriched fluorinated isostere of the iPr group is reported. The difluorination of readily accessible α-CF3-styrenes is enabled by the in situ generation of a chiral ArIF2 species to forge a stereocentre with the substituents F, CH2F and CF3 (up to 95 %, >20:1 vicinal:geminal difluorination). The replacement of the metabolically labile benzylic proton results in a highly preorganised scaffold as was determined by X-ray crystallography (π→σ* and stereoelectronic gauche σ→σ* interactions). A process of catalyst editing is disclosed in which preliminary validation of enantioselectivity is placed on a structural foundation.
Palladium-catalyzed Suzuki–Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes
Li, Yang,Zhao, Bo,Dai, Kun,Tu, Dong-Huai,Wang, Bo,Wang, Yao-Yu,Liu, Zhao-Tie,Liu, Zhong-Wen,Lu, Jian
, p. 5684 - 5690 (2016/08/23)
A mild and efficient palladium-catalyzed cross-coupling between fluorinated vinyl chloride and arylboronic acids is described. The use of ligand B successfully overcomes the strong electronic withdrawing of trifluoromethylated substrates and allows the efficient synthesis of a wide range of α and α,β-trifluoromethyl containing olefins. By using this method, the key intermediate for synthesis of Efavirenz can be obtained in a simple route. The efficient conversion of two freon molecules into useful α and α,β-trifluoromethyl containing olefins is a useful route in organic chemistry.
