An alternative approach to synthesize bis‐indolylmethanes (BIMs) via a unique p ‐toluenesulfonic acid (PTSA) catalyzed dual C sp3 −C sp2 bond‐breaking reaction has been reported here. In the reported protocol, 1,3,5‐trimethoxybenzene (TMB), an electron‐rich and sterically bulky arene, acts as a carbon‐based leaving group which can be recovered after the completion of the reaction. In this process, several BIMs of various indole derivatives can be synthesized from symmetrical triarylmethanes (TRAMs) containing bis‐TMB motifs. By modifying the reaction conditions, we could control the sequential bond cleavage of two C sp3 −C sp2 bonds in starting TRAM.
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Uddin et al. (2024) studied this question.
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