Oxidized arenol intermediates in intermolecular carbon-carbon bond formation. Naphthoid cyclohexa-2,4-dienones via oxidative nucleophilic substitution

[GRAPHICS] Dearomatization of arenes is a powerful strategy for the preparation of fun ctionalized cyclic olefins, Phenol oxidation can be exploited as a dearomat ization tactic to produce cyclohexa-2,4-dienones. lodine(lll)-mediated oxid ation of 2-alkyl- and 5-alkoxynaphthols was accomplished in the presence of an allylsilane or a silyl enol ether carbon-based nucleophile to furnish c yclohexa-2,4-dienone derivatives in moderate to good yields. This intermole cular carbon-carbon bond-forming reaction is particularly promising for the preparation of synthetically valuable naphthoid orthoquinols.