Remarkable access to fluoroalkylated trisubstituted alkenes via highly stereoselective cobalt-catalyzed hydrosilylation reaction of fluoroalkylated alkynes.
Hydrosilylation reaction of various fluoroalkylated alkynes with Et(3)SiH in the presence of a catalytic amount of Co(2)(CO)(8) was investigated. The hydrosilylation of the alkynes having fluoroalkyl and aryl groups took place smoothly with good regioselectivity (ca. 80:20). In sharp contrast, the reaction of the alkynes having a fluoroalkyl group and a benzyl-type substituent, or various propargyl alcohols gave the corresponding vinylsilanes in an excellent regio- and stereoselective manner. Treatment of the vinylsilanes with various aldehydes in the presence of Zn(OTf)(2) and TBAF afforded the coupling products in good yields.
Konno
Tsutomu
T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp
Taku
Ken-ichi
K
Yamada
Shigeyuki
S
Moriyasu
Kazuki
K
Ishihara
Takashi
T
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D017655:Silicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D006845:Hydrocarbons, Fluorinated; D017655:Silicon Compounds; D003035:Cobalt