Synthesis of porphyrin indolin-2-one conjugates via palladium-catalyzed amination reactions
authors Menezes, JCJMDS; Pereira, AMVM; Neves, MGPMS; Silva, AMS; Santos, SM; Martinez, ST; Silva, BV; Pinto, AC; Cavaleiro, JAS
nationality International
journal TETRAHEDRON
author keywords Porphyrin; Indolin-2-one; Palladium; Phosphine ligand; C-N coupling; Buchwald-Hartwig; Halogen position; Heating condition; B3LYP
keywords TOMENTOSA WILLD. DC; EFFICIENT SYNTHESIS; COUPLING REACTIONS; ARYL CHLORIDES; DERIVATIVES; TETRAPHENYLPORPHYRINS; DEHALOGENATION; INHIBITORS; BROMIDES; LIGANDS
abstract 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. (C) 2012 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4020
year published 2012
volume 68
issue 39
beginning page 8330
ending page 8339
digital object identifier (doi) 10.1016/j.tet.2012.07.024
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000308451500025
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journal impact factor 2.233
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