Palladium-Catalyzed Synthesis of (Z)-3-Arylthioacrylic Acids and Thiochromenones

Thiruvengadam Palani, Kyungho Park, Kwang Ho Song, Sunwoo Lee

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The three-component reaction of aryl halides, sodium sulfide pentahydrate (Na2S×5 H2O), and propiolic acid in the presence of 2.5% bis(triphenylphosphine)palladium chloride [Pd(PPh3) 2Cl2], 5% 1,4-bis(diphenylphosphino)butane (dppb) and 2equivalents of 1,8-diazabicycloundec-7-ene (DBU) produces stereoselectively (Z)-3-arylthioacrylic acids in good yields. A study of the reaction pathway suggested that the C-S bond formation between aryl halides and Na 2S×5 H2O proceeded first, and the resulting intermediate reacted with propiolic acid to produce the desired product. In addition, when the resulting product was treated with acid, the respective thiochromenones were formed in good yields.

Original languageEnglish
Pages (from-to)1160-1168
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number6
DOIs
Publication statusPublished - 2013 Apr 15

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Keywords

  • (Z)-alkenyl sulfides
  • cross-coupling
  • palladium
  • propiolic acid
  • thiochromenones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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