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

• Type: Article in International Scientific Journal
• Date: 2017

Authors

Pereira, AMVM (Author) FEUP; Lacerda, PSS (Author) Other; Silva, BNM (Author) Other; Neves, MGPMS (Author) Other; Silva, AMS (Author) Other; Silva, BV (Author) Other; da Silva, FC (Author) Other; Ferreira, VF (Author) Other; Pinto, AC (Author) Other; Cavaleiro, JAS (Author) Other

Journal

Title: Dyes and Pigments

Vol. 139

Pages: 247-254

ISSN: 0143-7208

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 3 Citations

Scopus - 9 Citations

Other information

Authenticus ID: P-00M-J92

DOI: 10.1016/j.dyepig.2016.12.010

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8