Article

Remarkable access to fluoroalkylated trisubstituted alkenes via highly stereoselective cobalt-catalyzed hydrosilylation reaction of fluoroalkylated alkynes.

Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
Organic & Biomolecular Chemistry (Impact Factor: 3.57). 04/2009; 7(6):1167-70. DOI: 10.1039/b819476a
Source: PubMed

ABSTRACT 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.

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May 31, 2014