Bromine-Radical-Mediated Synthesis of β-Functionalized β,γ- and δ,ϵ-Unsaturated Ketones via C-H Functionalization of Aldehydes

Takashi Kippo, Yuki Kimura, Mitsuhiro Ueda, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

The bromine-radical-mediated allylation reaction of aldehydes was studied. In the presence of V-65 as radical initiator, the reaction of aldehydes with allyl bromides gave β,γ-unsaturated ketones in good yields (13 examples, 45-84%). The reaction is triggered by hydrogen abstraction from the aldehyde by bromine radical to form an acyl radical, which undergoes an S H 2′-type addition-elimination reaction with allyl bromides to give coupling products with liberation of bromine radical. Three-component coupling reactions comprising aldehydes, electron-deficient alkenes, and methallyl bromide also proceeded to give δ,ϵ-unsaturated ketones.

Original languageEnglish
Pages (from-to)1733-1737
Number of pages5
JournalSynlett
Volume28
Issue number14
DOIs
StatePublished - 1 Sep 2017

Keywords

  • S 2′ reaction
  • bromine radical
  • three-component reaction
  • β,γ-unsaturated ketones
  • δ,ϵ-unsaturated ketones

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