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The First pincer-aryl [M–(NCN)] complexes {M = Pd(II); Pt(II)} with chiral pyridine donors: synthesis and catalytic activity in C–C bond formation

Soro, Barbara and Stoccoro, Sergio and Minghetti, Giovanni and Zucca, Antonio and Cinellu, Maria Agostina and Manassero, Mario and Gladiali, Serafino Gabriele (2006) The First pincer-aryl [M–(NCN)] complexes {M = Pd(II); Pt(II)} with chiral pyridine donors: synthesis and catalytic activity in C–C bond formation. Inorganica Chimica Acta, Vol. 359 (6), p. 1879-1888. ISSN 0020-1693. Article.

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DOI: 10.1016/j.ica.2005.07.045

Abstract

The first chiral bis(pyridine) N–C(H)–N pincer ligand, (5S,7S)-1,3-bis(6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanquinolin-2-yl)benzene (HL) has been synthesized and characterized by a thorough 1H NMR analysis. Reaction of HL with K2[PtCl4] in acetic acid gives [Pt(L)Cl] (1), where L acts as a tridentate N–C–N pincer ligand. The analogous palladium(II) derivatives [Pd(L)Cl] (2), and [Pd(L)(OAc)] (3), were first prepared through a transmetalation reaction between Pd(OAc)2 and the organomercury compound [Hg(L)Cl] (4). The structures of compounds 1 (Pt) and 2 (Pd), as determined by X-ray diffraction, are reported and compared. Compound 2 can also be obtained from Na2[PdCl4] and HL in refluxing acetic acid, i.e., under the same conditions used for compound 1. Apparently, this is the first palladium pincer derivative of a 1,3-bis(pyridyl)benzene ligand synthesized by direct C–H activation.
The neutral complexes 1–3 are catalysts of modest activity, but devoid of enantioselectivity in the Heck reaction between iodobenzene and methyl acrylate and in the aldol condensation of benzaldehyde with methyl isocyanoacetate.

Item Type:Article
ID Code:4033
Status:Published
Refereed:Yes
Uncontrolled Keywords:Chiral pyridine ligands, pincer complexes, palladium complexes, platinum complexes, crystal structures
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Elsevier
ISSN:0020-1693
Deposited On:17 Jun 2010 12:50

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