An efficient protocol for the stereoselective construction of multisubstituted fluorine-containing alkenes. A palladium-catalyzed bisstannylation of fluorinated internal alkynes.
On treatment of various fluorinated internal alkynes with 1.2 equiv of hexabutylditin under the influence of 2.5 mol % of Pd(t-BuNC)(2)Cl(2) in THF at room temperature for 4 h, the bisstannylation proceeded smoothly to afford the corresponding bisstannylated cis-adducts in high yields. Thus obtained adducts were subjected to the Stille cross-coupling reaction to give the corresponding tetrasubstituted fluorine-containing alkenes with defined stereochemistry in good yields.
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp
Tsutomu
T
Konno
Ryoko
R
Kinugawa
Atsunori
A
Morigaki
Takashi
T
Ishihara