One-pot synthesis of new isatin-porphyrin conjugates by the palladium Buchwald-Hartwig methodology involving β-aminoporphyrinatonickel(II) and 3-ketal isatin derivatives. (April 2017)

• Record Type: Journal Article
• Authors: Pereira, Ana M.V.M.; Lacerda, Paula S.S.; Silva, Bianca N.M.; Neves, Maria G.P.M.S.; Silva, Artur M.S.; Silva, Bárbara V.; da Silva, Fernando C.; Ferreira, Vitor F.; Pinto, Angelo C.; Cavaleiro, José A.S.
• Is Part Of: Dyes and pigments. Volume 139(2017)
• Page Start: 247
• Page End: 254
• Publication Date: 2017-04
• Subjects: Porphyrin -- Isatin -- Intracyclized derivatives -- C-N coupling -- Palladium -- Buchwald-Hartwig; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.12.010
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A simple methodology giving rise to a new series of isatin-porphyrin conjugates and corresponding intracyclized derivatives is described. Palladium-catalyzed amination reactions of iodinated isatin derivatives containing the 3-carbonyl group protected with ketal functionalities and 2-amino-5, 10, 15, 20-tetraphenylporphyrinatonickel(II) was the used procedure. The combination of palladium catalysts and the phosphine ligand dicyclohexylphospino-2′, 4′, 6'-triisopropylbiphenyl (XPhos) led to isatin-porphyrin conjugates in good yields. Nevertheless, the use of palladium acetate even resulted on the formation of additional six membered fused ring compounds. This brings a new perspective to access quinolino[2, 3, 4- at ]porphyrins, a set of compounds which are typically obtained by harsh Cadogan or thermal cyclization approaches. Graphical abstract: Highlights: One-pot palladium-catalyzed synthesis of new isatin-porphyrin conjugates. Quinolino[2, 3, 4- at ]porphyrin-isatin derivatives as new structural entities. Pd(OAc)2, XPhos and KO t Bu being the favorite catalyst. Novel molecular frameworks with potential medicinal and other applications.