Oxidative dearomatization of phenols and anilines via lambda(3)- and lambda(5)-iodane-mediated phenylation and oxygenation

Stéphane Quideau; Laurent Pouységu; Aurélie Ozanne; Julien Gagnepain

doi:10.3390/10010201

Oxidative dearomatization of phenols and anilines via lambda(3)- and lambda(5)-iodane-mediated phenylation and oxygenation

Molecules. 2005 Jan 31;10(1):201-16. doi: 10.3390/10010201.

Authors

Stéphane Quideau¹, Laurent Pouységu, Aurélie Ozanne, Julien Gagnepain

Affiliation

¹ Institut Européen de Chimie et Biologie and Laboratoire de Chimie des Substances Végétales, Centre de Recherche en Chimie Moléculaire, Université Bordeaux 1, France. [email protected]

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemistry*
Benzene / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / pharmacology
Cyclization / drug effects
Iodine Compounds / pharmacology*
Iodobenzenes / chemistry
Iodobenzenes / pharmacology
Models, Biological
Oxidation-Reduction
Oxygen / chemistry*
Phenols / chemistry*

Substances

Aniline Compounds
Bridged Bicyclo Compounds, Heterocyclic
Iodine Compounds
Iodobenzenes
Phenols
chloro(diphenyl)-lambda(3)-iodane
o-iodoxybenzoic acid
Benzene
Oxygen