Triarylmethyl Cation‐Catalyzed Three‐Component Coupling for the Synthesis of Unsymmetrical Bisindolylmethanes

An 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 couple...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-12, Vol.2021 (48), p.6737-6742
Main Authors: Patterson, William J., Lucas, Kelly, Jones, Vanessa A., Chen, Zhenghua, Bardelski, Kevin, Guarino‐Hotz, Melissa, Brindle, Cheyenne S.
Format: Article
Language:English
Subjects:
Aromatic substitution
Bisindolylmethanes
Carbocations
Cations
Environmental impact
Imines
Indoles
Lewis acids
Nucleophiles
Optimization
Organocatalysis
Selectivity
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Summary:An 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. Triarylmethyl cations catalyze the synthesis of unsymmetrical bisindolylmethanes from imines and two different indoles. Optimization of the catalyst by tuning cation stability allows for excellent single addition selectivity. The single addition intermediates can be isolated or used in situ in a high‐yielding one‐pot two‐step reaction to generate unsymmetrical bisindolylmethanes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100946