146560-61-4Relevant articles and documents
Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp3)?F Bonds
Xie, Ting,Zhang, Chen,Zhang, Si-Xuan,Rao, Weidong,Xu, Haiyan,Shen, Zhi-Liang,Chu, Xue-Qiang
, p. 4736 - 4743 (2020)
The strong and unreactive C?F bond makes polyfluorocarbons extremely long-lived and potentially toxic. A successive selective and controllable C(sp3)?F functionalization of polyfluoroalkylated ketones with S- and O-nucleophiles to enable efficient synthesis of pharmaceutically important fluorine- and sulfur-containing polycyclic furan and chromene derivatives under transition metal-free conditions is demonstrated here. The combination of C?S/C?O coupling, aromatization, and cyclization cascade contribute to the accurate four/five C(sp3)?F bond cleavage at two different sites of perfluoroalkyl chain. The formation of reactive quinoid intermediates and the necessity of using TBAB (tetrabutylammonium bromide) as additive and Cs2CO3 as base were identified by detailed mechanistic studies. (Figure presented.).
α-Fluoroalkylation of carbonyl compounds mediated by a highly reactive alkyl-rhodium complex
Sato, Kazuyuki,Yamazoe, Satoshi,Akashi, Yukiko,Hamano, Tetsuya,Miyamoto, Arisa,Sugiyama, Shuhei,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
experimental part, p. 86 - 90 (2010/03/26)
Treatment of silyl enol ethers of various carbonyl compounds with Et2Zn and fluoroalkyl halides (Rf-X) in the presence of RhCl(PPh3)3 in DME gave the corresponding α-Rf carbonyl compounds. A highly reactive alkyl-rhodium complex which was derived from RhCl(PPh3)3 and Et2Zn must be crucial in this reaction by accelerating the reaction rate and improving the yields dramatically. This reaction overcomes difficulties on the synthesis of α-Rf carbonyl compounds due to inverse polarization of Rf-X.
