A “Green” Route to Perylene Dyes: Direct Coupling Reactions of 1,8-Naphthalimide and Related Compounds under Mild Conditions Using a “New” Base Complex Reagent, <i>t</i>-BuOK/DBN

The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed

A “Green” Route to Perylene Dyes: Direct Coupling Reactions of 1,8-Naphthalimide and Related Compounds under Mild Conditions Using a “New” Base Complex Reagent, <i>t</i>-BuOK/DBN

The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed

Catalytic Activities of CuSO₄/Al₂O₃ in Dehydrogenation of Arenes by Dioxygen

The oxidation reactions of hydroquinones, 2-naphthols, or 2,6-di-tert-butylphenol efficiently occurred by catalysis with alumina-supported copper(II) sulfate to give the corresponding benzoquinones, 1,1‘-bi-2-naphthols, and 4,4‘-diphenoquinone, respectively, in good yields. The synthetic potentiality of the catalytic reactions was demonstrated by easy isolation of the final products using only filtration and solvent evaporation as well as by application to large-scale syntheses of the benzoquinones and binaphthols. The catalysis with alumina-supported copper(II) sulfate was also applied to the oxidative intramolecular coupling of 5,5‘-diacenaphthene to the corresponding perylene compound