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

• Type: Article in International Scientific Journal
• Date: 2012

Authors

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

Journal

Title: Tetrahedron

Vol. 68

Pages: 8330-8339

ISSN: 0040-4020

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 11 Citations

Scopus - 11 Citations

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10