title: Preparation of phenols by phthaloyl peroxide-mediated oxidation of arenes.
abstract: This protocol describes an approach to installing hydroxyls into arenes through the direct replacement of C-H bonds with C-O bonds. This direct oxidation avoids the need to prefunctionalize the substrate, use precious metals, introduce directing groups, or use strong Brønsted or Lewis acids. Phthaloyl peroxide, the sole reagent used for this transformation, can be prepared readily from the commodity chemicals phthaloyl chloride and sodium percarbonate. Phthaloyl peroxide oxidizes a diverse range of arenes, and the reactions that involve its use are characterized by high functional group compatibility, which enables the hydroxylation of simple arenes, advanced synthetic intermediates, natural products and other drug-like molecules forming the corresponding phenolic compounds. Notably, the reaction is operationally straightforward and has no special requirements for the exclusion of oxygen and water. The synthesis of phthaloyl peroxide takes 4  h and the subsequent hydroxylation of mesitylene takes 21  h.
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas, USA.
authors.forename: Changxia
authors.initials: C
authors.lastname: Yuan
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas, USA.
authors.forename: Anders M
authors.initials: AM
authors.lastname: Eliasen
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas, USA.
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Camelio
authors.affiliation: 1] Department of Chemistry, The University of Texas at Austin, Austin, Texas, USA. [2] Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California, USA.
authors.forename: Dionicio
authors.initials: D
authors.lastname: Siegel
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis; D060326:Chemistry Techniques, Synthetic; D006900:Hydroxylation; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*; D010636:Phenols / Q000138:chemical synthesis*; D010795:Phthalic Acids / Q000737:chemistry*; D013997:Time Factors
chemical_list: D001555:Benzene Derivatives; D010545:Peroxides; D010636:Phenols; D010795:Phthalic Acids; C000596643:phthaloyl peroxide; C010219:mesitylene