Synthesis of Symmetric Bis(N-alkylaniline)triarylmethanes via Friedel鈥揅rafts-Catalyzed Reaction between Secondary Anilines and Aldehydes

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• 作者：Rafael F. A. Gomes ; Jaime A. S. Coelho ; Raquel F. M. Frade ; Alexandre F. Trindade ; Carlos A. M. Afonso
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：10404-10411
• 全文大小：496K
• ISSN：1520-6904

文摘

The first general protocol for the preparation of symmetric triarylmethanes bearing secondary anilines by ytterbium-catalyzed Friedel鈥揅rafts 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 渭M.