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