Synthesis of porphyrin indolin-2-one conjugates via palladium-catalyzed amination reactions

• Tipo: Artigo em Revista Científica Internacional
• Data: 2012

Autores

Menezes, JCJMDS (Autor) Outra; Pereira, AMVM (Autor) Outra; Neves, MGPMS (Autor) Outra; Silva, AMS (Autor) Outra; Santos, SM (Autor) Outra; Martinez, ST (Autor) Outra; Silva, BV (Autor) Outra; Pinto, AC (Autor) Outra; Cavaleiro, JAS (Autor) Outra

Revista

Título: Tetrahedron

Vol. 68

Páginas: 8330-8339

ISSN: 0040-4020

Editora: Elsevier

Indexação

ISI Web of Knowledge - 11 Citações

Scopus - 11 Citações

Outras Informações

ID Authenticus: P-002-5BP

DOI: 10.1016/j.tet.2012.07.024

Abstract (EN): New porphyrin indolin-2-one conjugates were synthesized via palladium-catalyzed amination reactions of iodinated and dibrominated indolin-2-one derivatives with (2-amino-5,10,15.20-tetraphenylpor phyrinato)nickel(II). The combination of palladium catalysts and the phosphine ligand dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) is an effective methodology for catalyzing the coupling of 5-iodo-, 5,7-dibromo- and 4,6-dibromo-1,3,3-trimethylindolin-2-one with 2-aminoporphyrin to give the corresponding mono-(2-aminoporphyrinyl)- and di-(2-aminoporphyrinyl)-substituted indolin-2-ones in satisfactory yields under mild conditions. The mono brominated porphyrinic derivatives also underwent cross-coupling reactions under similar catalytic conditions. The studies also demonstrated that the course of the coupling process depends on factors, such as the catalytic system, number and position of the halogen substituents and the heating condition. Insights into the reactivity trends of the 5-iodo; 4,6- and 5,7-dibrominated indolin-2-one derivatives was carried out using theoretical calculations performed using density-functional theory with the B3LYP functional.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 10