4.8 Article

Synthesis of Isocoumarins through Three-Component Couplings of Arynes, Terminal Alkynes, and Carbon Dioxide Catalyzed by an NHC-Copper Complex

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 38, Pages 10213-10217

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404692

Keywords

alkynes; arynes; carbon dioxide; copper; multicomponent reactions

Funding

  1. Japan Society for the Promotion of Science (JSPS)
  2. Global COE Program (Chemistry Innovation through Cooperation of Science and Engineering)
  3. University of Tokyo
  4. Ministry of Education, Culture, Sports, Science and Technology (MEXT) (Japan)
  5. Japan Science and Technology Agency (JST)

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A copper-catalyzed multicomponent coupling reaction between in situ generated ortho-arynes, terminal alkynes, and carbon dioxide was developed to access isocoumarins in moderate to good yields. The key to this CO2-incorporating reaction was the use of a versatile N-heterocyclic carbene/copper complex that was able to catalyze multiple transformations within the three-component reaction.

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