Flow Giese reaction using cyanoborohydride as a radical mediator

Takahide Fukuyama, Takuji Kawamoto, Mikako Kobayashi, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Tin-free Giese reactions, employing primary, secondary, and tertiary alkyl iodides as radical precursors, ethyl acrylate as a radical trap, and sodium cyanoborohydride as a radical mediator, were examined in a continuous flow system. With the use of an automated flow microreactor, flow reaction conditions for the Giese reaction were quickly optimized, and it was found that a reaction temperature of 70 °C in combination with a residence time of 10-15 minutes gave good yields of the desired addition products.

Original languageEnglish
Pages (from-to)1791-1796
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - 3 Sep 2013

Keywords

  • Continuous flow system
  • Cyanoborohydride
  • Flow chemistry
  • Iodoalkanes
  • Microreactor
  • Tin-free Giese reaction

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