2-Fluoro-3-phenyl-allyltrimethylsilane: A new fluorinated reagent for Hosomi–Sakurai reaction

• Published in: Journal of fluorine chemistry Vol. 131; no. 6; pp. 709 - 713
• Main Authors: Hayashi, Tsuyoshi, Usuki, Yoshinosuke, Iio, Hideo
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.06.2010; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Hosomi–Sakurai reaction; Lewis acid-promoted allylation; Physical Sciences; Science & Technology; β-Fluorinated allylsilane; Lewis acid-promoted allylation; Hosomi–Sakurai reaction; β-Fluorinated allylsilane; Hosomi-Sakurai reaction; ALLYLSILANES; beta-Fluorinated allylsilane; BIOMIMETIC POLYENE CYCLIZATIONS
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2010.03.005

2-Fluoro-3-phenyl-allyltrimethylsilane, prepared from β-fluorinated allylic acetate via a π-allylpalladium intermediate, reacted with various aldehydes and acetals in the presence of TiCl 4 to afford the corresponding homoallyl alcohols and homoallyl ethers, respectively, in good to moderate yields. 2-Fluoro-3-phenyl-allyltrimethylsilane, prepared from β-fluorinated allylic acetate via a π-allylpalladium intermediate, reacted with various aldehydes and acetals in the presence of TiCl 4 to afford the corresponding homoallyl alcohols and homoallyl ethers, respectively, in good to moderate yields.