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

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

doi:10.1002/adsc.201201106

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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

33 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 language	English
Pages (from-to)	1160-1168
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	6
DOIs	https://doi.org/10.1002/adsc.201201106
Publication status	Published - 2013 Apr 15

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201201106

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title = "Palladium-Catalyzed Synthesis of (Z)-3-Arylthioacrylic Acids and Thiochromenones",

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.",

keywords = "(Z)-alkenyl sulfides, cross-coupling, palladium, propiolic acid, thiochromenones",

author = "Thiruvengadam Palani and Kyungho Park and Song, \{Kwang Ho\} and Sunwoo Lee",

year = "2013",

month = apr,

day = "15",

doi = "10.1002/adsc.201201106",

language = "English",

volume = "355",

pages = "1160--1168",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Palladium-Catalyzed Synthesis of (Z)-3-Arylthioacrylic Acids and Thiochromenones

AU - Palani, Thiruvengadam

AU - Park, Kyungho

AU - Song, Kwang Ho

AU - Lee, Sunwoo

PY - 2013/4/15

Y1 - 2013/4/15

N2 - 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.

AB - 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.

KW - (Z)-alkenyl sulfides

KW - cross-coupling

KW - palladium

KW - propiolic acid

KW - thiochromenones

UR - https://www.scopus.com/pages/publications/84876467456

U2 - 10.1002/adsc.201201106

DO - 10.1002/adsc.201201106

M3 - Article

AN - SCOPUS:84876467456

SN - 1615-4150

VL - 355

SP - 1160

EP - 1168

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 6

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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