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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: ryuc.s.osakafu-u.ac.jp

I. Ryu, S. Uehara, H. Hirao, T. Fukuyama, Org. Lett., 2008, 10, 1005-1008.

DOI: 10.1021/ol7031043 (free Supporting Information)


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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