Electron-deficient naphthalene diimides as efficient planar π-acid organocatalysts for selective oxidative C–C coupling of 2,6-di-tert-butylphenol: A temperature effect

• An efficient planar π-acid electron transfer organocatalyst for C–C coupling was demonstrated.
• It is first-time observation of the C–C coupling catalytic function for naphthene bisimides.
• The C–C coupling reaction products could be controlled by the reaction temperatures.
• An unexpected ring-rearranged trimeric quinone methide derivative has been synthesized in this method.

An efficient planar π-acid electron transfer organocatalyst based on electron-deficient substituted naphthalene diimide has been developed for oxidative C–C coupling of 2,6-di-tert-butylphenol to its dimeric derivative or unexpected ring-rearranged trimeric quinone methide by controlling the reaction temperatures.

Figure optionsDownload high-quality image (144 K)Download as PowerPoint slide