Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 38, Pages 11543-11547Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606359
Keywords
aerobic oxidation; aryl ethers; copper catalysis; ortho-quinones; phenols
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Funding
- Natural Sciences and Engineering Council of Canada (NSERC)
- Fonds de Recherche du Quebec-Nature et Technologies (FRQNT)
- FRQNT Center for Green Chemistry and Catalysis at McGill University
- NSERC CREATE Program in Green Chemistry at McGill University
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ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.
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