Synthesis of 2-Arylquinolines from 2-Iodoanilines and β-Chloropropiophenones via Palladium-Catalyzed Cascade Reaction

Jooyeon Yoon, Cheol-Hong Cheon

Research output: Contribution to journalArticle

Abstract

A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.

Original languageEnglish
JournalAsian Journal of Organic Chemistry
DOIs
Publication statusPublished - 2019 Jan 1

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Quinolines
Iridium
Palladium
Chlorides
2-iodobenzenamine
quinoline

Keywords

  • 2-Arylquinolines
  • Cascade reaction
  • Ligand free
  • Palladium
  • β-Chloropropiophenone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.",
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AU - Cheon, Cheol-Hong

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AB - A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.

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KW - Palladium

KW - β-Chloropropiophenone

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