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Gold(III) adducts with chiral pyridinyl-oxazolines: synthesis, reactivity of the coordinated ligands, and structural characterizations

Cinellu, Maria Agostina and Maiore, Laura and Minghetti, Giovanni and Stoccoro, Sergio and Zucca, Antonio and Manassero, Mario and Manassero, Carlo (2009) Gold(III) adducts with chiral pyridinyl-oxazolines: synthesis, reactivity of the coordinated ligands, and structural characterizations. Organometallics, Vol. 28 (24), p. 7015-7024. eISSN 1520-6041. Article.

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DOI: 10.1021/om900841b

Abstract

Novel gold(III) pyridinyl-oxazoline cationic complexes [Au(pyoxR)Cl2][X] [pyoxR = (S)-4-R-2-(pyridin-2-yl)-4,5-dihydrooxazole, with R = iPr, Bn, and (R)-4-phenyl-2-(pyridin-2-yl)-4,5-dihydrooxazole; X = PF6, AuCl4, or mixtures of the two anions] were synthesized and structurally characterized. Reaction of the adducts with NaOAc in aqueous solution afforded the neutral complexes [Au(N,N′,O)Cl] of the deprotonated ligands N-(1-hydroxy-3-R-2-yl)pyridine-2-carboxamide (R = iPr, Ph), N,N′H,OH, resulting from ring-opening of the bound pyox ligand by hydroxide ions and incorporation of hydroxide into the ring-opened products. Reaction of [Au(N,N′,O)Cl] (R = iPr) with HX (X = Cl, BF4, OTf) in aqueous solution resulted in protonation of the coordinated alkoxo group and its displacement from the coordination sphere to give the adducts [Au(N,N′,OH)ClX] (X = OTf, Cl) or the aquo complex [Au(N,N′,OH)(OH2)Cl]+ (X = BF4). Crystal structure characterizations were carried out on both [Au(N,N′,O)Cl] and [Au(N,N′,OH)Cl2] (R = iPr). Equimolar mixtures of the ring-opened derivative [Au(N,N′,O)Cl] (R = iPr) and either silver salts or HBF4 were found to promote, under mild conditions, polymerization of styrenes.

Item Type:Article
ID Code:3781
Status:Published
Refereed:Yes
Uncontrolled Keywords:Chiral pyridinyl-oxazolines, cationic gold(III) derivatives, coordinated ligands, catalytical activity
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:American Chemical Society
eISSN:1520-6041
Deposited On:29 Apr 2010 12:28

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