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Atmospheric Pressure of CO sub(2) as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes

Carbon dioxide (CO sub(2)) has been wildly employed as an environmentally benign C sub(1) resource for organic synthesis in the recent years. The capture of CO sub(2) with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant... Full description

Journal Title: Advanced Synthesis & Catalysis January 2016, Vol.358(1), pp.90-97
Main Author: Yu, Bing
Other Authors: Cheng, Bin-Bin , Liu, Wei-Qi , Li, Wei , Wang, Shan-Shan , Cao, Jie , Hu, Chang-Wen
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1615-4150 ; E-ISSN: 1615-4169 ; DOI: 10.1002/adsc.201500921
Link: http://search.proquest.com/docview/1800474428/
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title: Atmospheric Pressure of CO sub(2) as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes
format: Article
creator:
  • Yu, Bing
  • Cheng, Bin-Bin
  • Liu, Wei-Qi
  • Li, Wei
  • Wang, Shan-Shan
  • Cao, Jie
  • Hu, Chang-Wen
subjects:
  • Reagents
  • Alkynes
  • Carbon Capture and Storage
  • Catalysts
  • Synthesis
  • Carbon Dioxide
  • Amines
  • Aldehydes
  • Miscellaneous Sciences (So)
ispartof: Advanced Synthesis & Catalysis, January 2016, Vol.358(1), pp.90-97
description: Carbon dioxide (CO sub(2)) has been wildly employed as an environmentally benign C sub(1) resource for organic synthesis in the recent years. The capture of CO sub(2) with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant for the synthesis of oxazolidin-2-ones via the reaction with aromatic aldehydes and aromatic terminal alkynes. A variety of oxazolidin-2-ones with different functional groups were synthesized in 68-91% yields with only a 5mol% amount of CuI as catalyst. It was found that the synergetic effect of iodide is important for the transformation. Notable, the captured CO sub(2) serves not only as a protecting reagent for electron-rich primary amine to avoid catalyst poisoning, but also as a reactant for the construction of oxazolidin-2-ones.
language: eng
source:
identifier: ISSN: 1615-4150 ; E-ISSN: 1615-4169 ; DOI: 10.1002/adsc.201500921
fulltext: fulltext
issn:
  • 16154150
  • 1615-4150
  • 16154169
  • 1615-4169
url: Link


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titleAtmospheric Pressure of CO sub(2) as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes
creatorYu, Bing ; Cheng, Bin-Bin ; Liu, Wei-Qi ; Li, Wei ; Wang, Shan-Shan ; Cao, Jie ; Hu, Chang-Wen
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subjectReagents ; Alkynes ; Carbon Capture and Storage ; Catalysts ; Synthesis ; Carbon Dioxide ; Amines ; Aldehydes ; Miscellaneous Sciences (So)
descriptionCarbon dioxide (CO sub(2)) has been wildly employed as an environmentally benign C sub(1) resource for organic synthesis in the recent years. The capture of CO sub(2) with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant for the synthesis of oxazolidin-2-ones via the reaction with aromatic aldehydes and aromatic terminal alkynes. A variety of oxazolidin-2-ones with different functional groups were synthesized in 68-91% yields with only a 5mol% amount of CuI as catalyst. It was found that the synergetic effect of iodide is important for the transformation. Notable, the captured CO sub(2) serves not only as a protecting reagent for electron-rich primary amine to avoid catalyst poisoning, but also as a reactant for the construction of oxazolidin-2-ones.
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titleAtmospheric Pressure of CO sub(2) as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes
descriptionCarbon dioxide (CO sub(2)) has been wildly employed as an environmentally benign C sub(1) resource for organic synthesis in the recent years. The capture of CO sub(2) with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant for the synthesis of oxazolidin-2-ones via the reaction with aromatic aldehydes and aromatic terminal alkynes. A variety of oxazolidin-2-ones with different functional groups were synthesized in 68-91% yields with only a 5mol% amount of CuI as catalyst. It was found that the synergetic effect of iodide is important for the transformation. Notable, the captured CO sub(2) serves not only as a protecting reagent for electron-rich primary amine to avoid catalyst poisoning, but also as a reactant for the construction of oxazolidin-2-ones.
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titleAtmospheric Pressure of CO sub(2) as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes
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abstractCarbon dioxide (CO sub(2)) has been wildly employed as an environmentally benign C sub(1) resource for organic synthesis in the recent years. The capture of CO sub(2) with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant for the synthesis of oxazolidin-2-ones via the reaction with aromatic aldehydes and aromatic terminal alkynes. A variety of oxazolidin-2-ones with different functional groups were synthesized in 68-91% yields with only a 5mol% amount of CuI as catalyst. It was found that the synergetic effect of iodide is important for the transformation. Notable, the captured CO sub(2) serves not only as a protecting reagent for electron-rich primary amine to avoid catalyst poisoning, but also as a reactant for the construction of oxazolidin-2-ones.
doi10.1002/adsc.201500921
urlhttp://search.proquest.com/docview/1800474428/
date2016-01-07