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Herein, we report an efficient and simple copper-catalyzed oxidative diarylthiolation of maleimides with sulfur powder and aryl boronic acids, in which S powder was used as a substrate and internal oxidant. The corresponding double C-S bonds coupling products were obtained in moderate to high yields under a simple catalytic system. Mechanistic studies indicated that copper-catalyzed radical thiolation of aryl boronic acids with S powder, and the resulting arylthiyl underwent radical addition with double bonds of maleimides.