Journal
CHEMICAL SCIENCE
Volume 4, Issue 3, Pages 1287-1292Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc22318j
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec
- Boehringer Ingelheim (Canada) Ltd
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Treatment of phenols or anilines containing a sulfonyl group in the presence of a hypervalent iodine reagent promotes a formal dearomatizing [2 + 3] cycloaddition reaction on unactivated benzene and naphthalene derivatives. This process occurs via an intramolecular nucleophilic addition to the Wheland species generated during the oxidative activation. Subsequent treatment under acidic conditions readily transforms the tricyclic system into a biaryl via a formal cross-coupling process.
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