881682-70-8Relevant academic research and scientific papers
Preparation and addition-elimination reactions of benzyl α,β,β-trifluoroacrylate. A new stereoselective approach to (Z)-β-substituted α,β-difluoroacrylates
Yamada, Shigeyuki,Noma, Mayumi,Hondo, Kazunori,Konno, Tsutomu,Ishihara, Takashi
, p. 522 - 528 (2008/09/17)
(Chemical Equation Presented) Benzyl α,β,β- trifluoroacrylate (1) was prepared in good yield via the reductive Br-F elimination of benzyl 2-bromo-2,3,3,3-tetrafluoropropanoate or the palladium-catalyzed cross-coupling reaction of 1,2,2-trifluorovinylstannane with benzyl chloroformate. On treating 1 with various Grignard reagents or dialkylzinc reagents in the presence of copper(I) salt, the corresponding β-substituted α,β-difluoroacrylates were obtained in high yields with high Z-selectivity. Additionally, trialkylaluminum reagents were also found to be good nucleophiles, the corresponding addition-elimination products being afforded in good yields but with low stereoselectivity.
Novel synthesis of (Z)-difluoroacrylates via a highly stereoselective addition-elimination reaction
Yamada, Shigeyuki,Noma, Mayumi,Konno, Tsutomu,Ishihara, Takashi,Yamanaka, Hiroki
, p. 843 - 845 (2007/10/03)
On treating readily prepared benzyl 2,3,3-trifluoroacrylate with various Grignard reagents, e.g., aryl-, alkyl-, or alkenylmagnesium halide, in the presence of a catalytic amount of copper(I) salt in THF at -78 °C for 1 h, the corresponding α,β-difluoroacrylates were obtained in 54-98% yields with high Z-selectivity.
