Tin-Free Giese Reaction and the Related Radical Carbonylation Using Alkyl Iodides and Cyanoborohydrides
Ilhyong Ryu,* Shohei Uehara, Hidefumi Hirao and Takahide Fukuyama
*Department of Chemistry, Graduate School of Science, Osaka
Prefecture University, Sakai, Osaka 599-8531, Japan, Email: ryu
c.s.osakafu-u.ac.jp
I. Ryu, S. Uehara, H. Hirao, T. Fukuyama, Org. Lett., 2008, 10, 1005-1008.
DOI: 10.1021/ol7031043
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Abstract
Tin-free Giese reaction of alkyl iodides with electron-deficient alkenes and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. Transfer of iodine followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.
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proposed mechanism
Key Words
Giese Reaction, esters, ketones, sodium cyanoborohydride
ID: J54-Y2008-0700
