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Synthesis of Symmetric Bis(N‑alkylaniline)triarylmethanes via Friedel–Crafts-Catalyzed Reaction between Secondary Anilines and Aldehydes

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journal contribution
posted on 16.10.2015, 00:00 by Rafael F. A. Gomes, Jaime A. S. Coelho, Raquel F. M. Frade, Alexandre F. Trindade, Carlos A. M. Afonso
The first general protocol for the preparation of symmetric triarylmethanes bearing secondary anilines by ytterbium-catalyzed Friedel–Crafts reaction of hetero­(aryl) aldehydes and secondary anilines is reported. Mechanistic studies indicated that the iminium ion intermediate is the electrophilic partner. The reaction is greatly accelerated by high pressure (9 kbar) and showed a broad substrate scope on the hetero­(aryl) aldehyde. The new triarylmethanes exhibited activity against HT-29 cancer cell lines, with the best result scoring an IC50 of 1.74 μM.