Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 6, Pages 1694-1699Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811729
Keywords
boranes; 1; 3-dienes; hydroarylation; phenols; synthetic methods
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Funding
- National Natural Science Foundation of China [21333004, 21673110, 21572099, 21833002]
- China Postdoctoral Science Foundation [2017M620198]
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A B(C6F5)(3)-catalyzed hydroarylation of a series of 1,3-dienes with various phenols has been established through a combination of theoretical and experimental investigations, affording structurally diverse ortho-allyl phenols. DFT calculations show that the reaction proceeds through a borane-promoted protonation/Friedel-Crafts pathway involving a -complex of a carbocation-anion contact ion pair. This protocol features simple and mild reaction conditions, broad functional-group tolerance, and low catalyst loading. The obtained ortho-allyl phenols could be further converted into flavan derivatives using B(C6F5)(3) with good cis diastereoselectivity. Furthermore, this transformation was applied in the late-stage modification of pharmaceutical compounds.
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