4.8 Article

Carbon Dioxide Triggered and Copper-Catalyzed Domino Reaction: Efficient Construction of Highly Substituted 3(2H)-Furanones from Nitriles and Propargylic Alcohols

Journal

ORGANIC LETTERS
Volume 13, Issue 20, Pages 5520-5523

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202241r

Keywords

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Funding

  1. National Natural Science Foundation of China [20932002]
  2. National Basic Research Program of China (973 Program) [2010CB-732206]
  3. Ministry of Education of China [20090172110014]
  4. Guangdong Natural Science Foundation [10351064101000000]
  5. Fundamental Research Funds for the Central Universities [2011ZZ007]

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A novel carbon dioxide triggered and copper-catalyzed domino reaction for the efficient synthesis of highly substituted 3(2H)-furanones from readily available nitriles and propargylic alcohols has been developed. Carbon dioxide is a prerequisite for achieving the present catalytic transformation, and one of the oxygen atoms of carbon dioxide is incorporated into the 3(2H)-furanones. Nitriles not only act as the reaction solvent but also as the reactant; copper salts play dual roles of activating both the propargylic alcohols and nitriles.

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