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Recyclable and reusable PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes

PdCl 2 (PPh 3 ) 2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 C w... Full description

Journal Title: Green Chemistry 2014, Vol.16(5), pp.2515-2522
Main Author: Zhao, Hong
Other Authors: Cheng, Mingzhu , Zhang, Jiatao , Cai, Mingzhong
Format: Electronic Article Electronic Article
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ID: ISSN: 1463-9262 ; E-ISSN: 1463-9270 ; DOI: 10.1039/c3gc42278j
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title: Recyclable and reusable PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
format: Article
creator:
  • Zhao, Hong
  • Cheng, Mingzhu
  • Zhang, Jiatao
  • Cai, Mingzhong
subjects:
  • Carbon Monoxide
  • Iodides
  • Terminals
  • Aromatic Compounds
  • Chemical Reactions
  • Alkynes
  • Recycled
  • Carbonyls
  • Chemical and Electrochemical Properties (MD)
  • Chemical and Electrochemical Properties (Ep)
  • Chemical and Electrochemical Properties (Ed)
  • Chemical and Electrochemical Properties (EC)
ispartof: Green Chemistry, 2014, Vol.16(5), pp.2515-2522
description: PdCl 2 (PPh 3 ) 2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 C with Et 3 N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o -iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system can be easily recycled and reused six times without any loss of catalytic activity.
language:
source:
identifier: ISSN: 1463-9262 ; E-ISSN: 1463-9270 ; DOI: 10.1039/c3gc42278j
fulltext: fulltext
issn:
  • 1463-9262
  • 1463-9270
  • 14639270
  • 14639262
url: Link


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titleRecyclable and reusable PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
creatorZhao, Hong ; Cheng, Mingzhu ; Zhang, Jiatao ; Cai, Mingzhong
ispartofGreen Chemistry, 2014, Vol.16(5), pp.2515-2522
identifier
descriptionPdCl 2 (PPh 3 ) 2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 C with Et 3 N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o -iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system can be easily recycled and reused six times without any loss of catalytic activity.
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subjectCarbon Monoxide ; Iodides ; Terminals ; Aromatic Compounds ; Chemical Reactions ; Alkynes ; Recycled ; Carbonyls ; Chemical and Electrochemical Properties (MD) ; Chemical and Electrochemical Properties (Ep) ; Chemical and Electrochemical Properties (Ed) ; Chemical and Electrochemical Properties (EC);
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titleRecyclable and reusable PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
descriptionPdCl 2 (PPh 3 ) 2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 C with Et 3 N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o -iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system can be easily recycled and reused six times without any loss of catalytic activity.
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titleRecyclable and reusable PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
authorZhao, Hong ; Cheng, Mingzhu ; Zhang, Jiatao ; Cai, Mingzhong
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atitleRecyclable and reusable PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
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abstractPdCl 2 (PPh 3 ) 2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 C with Et 3 N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o -iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl 2 (PPh 3 ) 2 /PEG-2000/H 2 O system can be easily recycled and reused six times without any loss of catalytic activity.
doi10.1039/c3gc42278j
pages2515-2522
date2014-04-22