title: A biomimetic catalytic aerobic functionalization of phenols.
abstract: The importance of aromatic C-O, C-N, and C-S bonds necessitates increasingly efficient strategies for their formation. Herein, we report a biomimetic approach that converts phenolic C-H bonds into C-O, C-N, and C-S bonds at the sole expense of reducing dioxygen (O2) to water (H2O). Our method hinges on a regio- and chemoselective copper-catalyzed aerobic oxygenation to provide ortho-quinones. ortho-Quinones are versatile intermediates, whose direct catalytic aerobic synthesis from phenols enables a mild and efficient means of synthesizing polyfunctional aromatic rings.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8 (Canada).
authors.forename: Kenneth Virgel N
authors.initials: KV
authors.lastname: Esguerra
authors.forename: Yacoub
authors.initials: Y
authors.lastname: Fall
authors.forename: Jean-Philip
authors.initials: JP
authors.lastname: Lumb
mesh_terms: D032701:Biomimetics; D002384:Catalysis; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*
chemical_list: D010636:Phenols
keywords: copper; ortho-quinones; oxidation; synthetic methods; tyrosinase