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

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 comple...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-09, Vol.53 (38), p.10213-10217
Main Authors: Yoo, Woo-Jin, Nguyen, Thanh V. Q., Kobayashi, Shū
Format: Article
Language:English
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Summary: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. A facile synthetic protocol to isocoumarins consists of a three‐component coupling reaction between 1‐alkynes, 2‐(trimethylsilyl)aryl triflates, and CO2 (see scheme). The key to this reaction was the use of a versatile N‐heterocyclic carbene/copper complex that was able to catalyze multiple transformations within the three‐component reaction.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201404692