title: Organocatalytic Dakin oxidation by nucleophilic flavin catalysts.
abstract: Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.
authors.affiliation: The University of Texas at Arlington, Department of Chemistry and Biochemistry, Arlington, Texas 76019-0065, USA.
authors.forename: Shuai
authors.initials: S
authors.lastname: Chen
authors.forename: Mohammad S
authors.initials: MS
authors.lastname: Hossain
authors.forename: Frank W
authors.initials: FW
authors.lastname: Foss
mesh_terms: D000098:Acetophenones / Q000737:chemistry*; D002384:Catalysis; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D005415:Flavins / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000098:Acetophenones; D002396:Catechols; D005415:Flavins; D010636:Phenols; C087908:2'-hydroxyacetophenone