A versatile and efficient method for the coupling of maleimides and indoles at the C7‐position has been established under Rh(III) catalysis. The present protocol was compatible with various functional groups, diverse 3‐(indol‐7‐yl)maleimides and 3‐(indol‐7‐yl)succinimides were obtained in moderate to excellent yields by switching reaction conditions. Moreover, this method further highlights the unique practical application for the conjugation with pharmaceutically useful compounds and amino acid derivatives. To explore the mechanism of this transformation, deuteration studies and control experiments have been carried out.

A new, simple, and metal-free route for the diselenation of maleimides has been first developed employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature. The present method is compatible with different functional groups, and various diselenyl maleimides were obtained in moderate to excellent yields. Moreover, this protocol further highlights the unique practical application for the functionalization of biologically relevant molecules and amino acid derivatives. Preliminary mechanism studies suggest that radicals may be involved in this novel transformation. Additionally, this protocol is also applicable for the monoselenation of maleimides by switching the reaction conditions and selenation of other electron-deficient alkenes.

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