Carbon-carbon bond-formation by aminocatalytic nucleophilic addition to aryl aldehyde ideally generates addition-elimination product. Here, we report an unexpected, yet efficient aminocatalytic nucleophilic addition of indole to aryl aldehydes to synthesize pharmacologically important bis(indolyl)methanes via aminocatalytic addition substitution reaction. Although many acid catalysed synthesis are reported, this is the first aminocatalytic synthesis of bis(indolyl)methanes. Graphic Abstract First aminocatalytic synthesis of bis(indolyl)methanes and DFT studies on the reaction pathway. Grace Basumatary, Rahul Mohanta, Satyajit Dey Baruah, Ramesh Ch. Deka, and Ghanashyam Bez. [GRAPHICS] .