Oxidative dearomatization of phenols and anilines via lambda(3)- and lambda(5)-iodane-mediated phenylation and oxygenation.
Treatment of 2-methylphenols with chloro(diphenyl)-lambda(3)-iodane led to their regioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via a proposed ligand coupling reaction. In the same vein of investigation, treatment of 2-methylanilines with the lambda(5)-iodane 2-iodoxybenzoic acid IBX reagent led to their regioselective dearomatization into previously undescribed ortho-quinol imines.
Quideau
Stéphane
S
Institut Européen de Chimie et Biologie and Laboratoire de Chimie des Substances Végétales, Centre de Recherche en Chimie Moléculaire, Université Bordeaux 1, France. s.quideau@iecb.u-bordeaux.fr
Pouységu
Laurent
L
Ozanne
Aurélie
A
Gagnepain
Julien
J
D000814:Aniline Compounds / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000494:pharmacology; D003500:Cyclization / Q000187:drug effects; D017613:Iodine Compounds / Q000494:pharmacology*; D007462:Iodobenzenes / Q000737:chemistry / Q000494:pharmacology; D008954:Models, Biological; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*
D000814:Aniline Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D017613:Iodine Compounds; D007462:Iodobenzenes; D010636:Phenols; C526016:chloro(diphenyl)-lambda(3)-iodane; C476101:o-iodoxybenzoic acid; D001554:Benzene; D010100:Oxygen