Tin-free giese reaction and the related radical carbonylation using Alkyl iodides and cyanoborohydrides

Ilhyong Ryu*, Shohei Uehara, Hidefumi Hirao, Takahide Fukuyama

*Corresponding author for this work

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)1005-1008
Number of pages4
JournalOrganic Letters
Volume10
Issue number5
DOIs
StatePublished - 6 Mar 2008

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