Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes

Takashi Kippo, Kanako Hamaoka, Mitsuhiro Ueda, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The full scope (30 examples) of the radical bromoallylation of alkynes using allyl bromides was studied. In this reaction, bromine radical adds to alkynes to form vinyl radicals, which then undergo an SH2′ reaction with allyl bromides to produce good yields of 1-bromo-1,4-dienes with the liberation of a bromine radical, which creates a radical chain. The sp2-carbon–bromine bond of the product dienes was further functionalized via cross-coupling and carbonylation reactions.

Original languageEnglish
Pages (from-to)7866-7874
Number of pages9
JournalTetrahedron
Volume72
Issue number48
DOIs
StatePublished - 1 Jan 2016

Keywords

  • Alkynes
  • Allyl bromides
  • Bromoallylation
  • Dienes
  • Radical reaction

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