Oxidative cycloaddition and cross-coupling processes on unactivated benzene derivatives
2013; Royal Society of Chemistry; Volume: 4; Issue: 3 Linguagem: Inglês
10.1039/c2sc22318j
ISSN2041-6539
AutoresGuillaume Jacquemot, Marc-André Ménard, Chloé L’Homme, Sylvain Canesi,
Tópico(s)Alkaloids: synthesis and pharmacology
ResumoTreatment 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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