Abstract
AbstractAn efficient synthesis of unsymmetrical bisindolylmethanes has been accomplished using triarylmethyl cations to catalyze the reaction of N‐arylimines with two different indoles. Optimization of the organocatalyst by tuning cation stability allows for excellent single addition selectivity when coupled with p‐nitrophenyl imines. The optimal catalyst is commercially available, and the reaction minimizes waste and environmental impact by employing a one‐to‐one ratio of starting materials. The intermediates can be isolated or used in situ in a one‐pot two‐step reaction to generate unsymmetrical bisindolylmethanes in high yields. The reaction tolerates a broad range of imines with the highest yields observed for electron‐poor and neutral imines. A wide range of indole nucleophiles are also successfully employed allowing for the creation of a large variety of unsymmetrical bisindolylmethanes.
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