Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes.
Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be <1 × 10(4) M(-1) s(-1) at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.
Department of Chemistry, Graduate School of Science, Osaka Prefecture University , Sakai, Osaka 599-8531, Japan.
Takuji
T
Kawamoto
Shohei
S
Uehara
Hidefumi
H
Hirao
Takahide
T
Fukuyama
Hiroshi
H
Matsubara
Ilhyong
I
Ryu
D000475:Alkenes / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry*; D004583:Electrons; D005609:Free Radicals / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure
D000475:Alkenes; D001894:Borohydrides; D005609:Free Radicals; D006847:Hydrocarbons, Iodinated; C009282:sodium cyanoborohydride