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

• Published in: Dyes and pigments 2017-04, Vol.139, p.247-254
• Main 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.
• Format: Article
• Language: English
• Subjects: Buchwald-Hartwig; C-N coupling; Intracyclized derivatives; Isatin; Palladium; Porphyrin
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2016.12.010

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. [Display omitted] •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 KOtBu being the favorite catalyst.•Novel molecular frameworks with potential medicinal and other applications.