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Tin-Free Giese Reaction and the Related Radical Carbonylation Using Alkyl Iodides and Cyanoborohydrides

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journal contribution
posted on 06.03.2008, 00:00 by Ilhyong Ryu, Shohei Uehara, Hidefumi Hirao, Takahide Fukuyama
Tin-free Giese reaction and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. The reaction took place chemoselectively at the carbon−iodine bond but not at the carbon−bromine and carbon−chlorine bonds. The iodine atom transfer followed by hydride reduction of the resulting carbon−iodine bond is proposed as a possible mechanism.