Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes

Takuji Kawamoto, Shohei Uehara, Hidefumi Hirao, Takahide Fukuyama, Hiroshi Matsubara, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)3999-4007
Number of pages9
JournalJournal of Organic Chemistry
Volume79
Issue number9
DOIs
StatePublished - 2 May 2014

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