Abstract
Dearomatization of arenes is a powerful strategy for the preparation of functionalized cyclic olefins. Phenol oxidation can be exploited as a dearomatization tactic to produce cyclohexa-2,4-dienones. Iodine(III)-mediated oxidation of 2-alkyl- and 2-alkoxynaphthols was accomplished in the presence of an allylsilane or a silyl enol ether carbon-based nucleophile to furnish cyclohexa-2,4-dienone derivatives in moderate to good yields. This intermolecular carbon−carbon bond-forming reaction is particularly promising for the preparation of synthetically valuable naphthoid orthoquinols.
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