We describe an alternative and more sustainable method for the synthesis of 2,2’-disubstituted 3,3’-biindoles starting from 2,2’-diaminotolanes and (hetero)arylaldehydes. The key feature of the approach is the use of an acidic Deep Eutectic Solvent (DES) able to exploit a double activity, i. e., solvent and Brønsted Acid (BA) catalyst, avoiding the use of Volatile Organic Compounds (VOCs) as solvents and additional acid catalysts. By this way, we synthesized twenty-five biindoles, including eighteen new compounds. The reactions run quickly under mild conditions by microwave heating at 70 °C, with yields ranging from good to very good. The reaction scope is rather broad. The medium demonstrated to be reusable at least five times with only a slight reduction in yields. Based on experimental evidence and previous literature findings, a plausible mechanism is proposed.
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