C−H Functionalization of 1,4-Naphthoquinone by Oxidative Coupling with Anilines in the Presence of a Catalytic Quantity of Copper(II) Acetate

• Published in: Journal of organic chemistry Vol. 76; no. 13; pp. 5264 - 5273
• Main Authors: Lisboa, Cinthia da S, Santos, Vanessa G, Vaz, Boniek G, de Lucas, Nanci C, Eberlin, Marcos N, Garden, Simon J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.2011; Amer Chemical Soc
• Subjects: Aniline Compounds - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Exact sciences and technology; General and physical chemistry; Molecular Structure; Naphthoquinones - chemical synthesis; Naphthoquinones - chemistry; Noncondensed benzenic compounds; Organic chemistry; Organometallic Compounds - chemistry; Oxidation-Reduction; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; ELECTRONIC ABSORPTION-SPECTRA; QUINONE CHEMISTRY; TETRAHYDROISOQUINOLINE ALKALOIDS; NUCLEOPHILIC-SUBSTITUTION; NAPHTHOQUINONE COLORING MATTERS; LAVENDAMYCIN ANALOGS; (-)-CRIBROSTATIN-4 RENIERAMYCIN-H; METAL-IONS; IONIZATION MASS-SPECTROMETRY; MARINE SPONGE; Catalytic reaction; Amine; Functionalization; Benzenic compound; Aromatic compound; Aniline derivatives; Oxidation; Copper II Acetate; Oxidative coupling; Catalyst
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo200354u

The oxidative addition of anilines (2) with 1,4-naphthoquinone (3) to give N-aryl-2-amino-1,4-naphthoquinones (1) was found to be catalyzed by copper(II) acetate. In the absence of the catalyst, the reactions are slower and give lower yields with the formation of many colateral products. In the presence of 10 mol % hydrated copper(II) acetate, the reactions are generally more efficient in that they are cleaner, higher yielding, and faster.