title: Synthesis of Symmetric Bis(N-alkylaniline)triarylmethanes via Friedel-Crafts-Catalyzed Reaction between Secondary Anilines and Aldehydes.
abstract: 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.
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon , Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Rafael F A
authors.initials: RF
authors.lastname: Gomes
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon , Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Jaime A S
authors.initials: JA
authors.lastname: Coelho
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon , Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Raquel F M
authors.initials: RF
authors.lastname: Frade
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon , Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Alexandre F
authors.initials: AF
authors.lastname: Trindade
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon , Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Carlos A M
authors.initials: CA
authors.lastname: Afonso