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Cyclopalladation of 6-substituted-2,2‘-bipyridines: metalation of unactivated methyl groups vs aromatic C−H activation

Zucca, Antonio and Cinellu, Maria Agostina and Pinna, Maria Vittoria and Stoccoro, Sergio and Minghetti, Giovanni (2000) Cyclopalladation of 6-substituted-2,2‘-bipyridines: metalation of unactivated methyl groups vs aromatic C−H activation. Organometallics, Vol. 19 (21), p. 4295-4304. eISSN 1520-6041. Article.

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DOI: 10.1021/om000239o

Abstract

6-Alkyl-2,2'-bipyridines, HL, (N2C10H7R; R ) CH2Me, HLet; CHMe2, HLip; CMe3, HLtb, CH2- CMe3, HLnp, CMe2Ph, HLdm) react with Na2[PdCl4] to give either 1:1 adducts [Pd(HL)Cl2] (HLet, HLip, HLnp) or cyclometalated complexes [Pd(L)Cl] (HLtb, HLdm). Reaction of palladium- (II) acetate, followed by exchange with LiCl, affords a series of cyclopalladated species [Pd- (L)Cl] where L is a terdentate anionic N-N-C ligand which originates from HL through direct activation of a C(sp3)-H or a C(sp2)-H bond. The structures of [Pd(Ltb)Cl] and [Pd- (Lnp)Cl], which contain a [5,5] or a [5,6] fused ring system, respectively, have been determined by X-ray diffraction and are compared. In the case of the ligand HLip, three different cyclometalated species have been isolated, [Pd(L)Cl], [Pd(L)Cl]2, and [Pd{N2C10H7[CH(CH2- OC(O)CH3)(CH2)]}Cl], the latter one arising from activation of both methyl groups of the substituent. The isolation of two [Pd(Ldm)Cl] species (compounds 8 and 9), having an aromatic or an aliphatic carbon-metal bond, respectively, is an example of isomerism, still rare in organometallic chemistry.

Item Type:Article
ID Code:5351
Status:Published
Refereed:Yes
Uncontrolled Keywords:Cyclopalladation, N donor ligands, new adducts, palladium, 2,2'-bipyridine
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:27 Jan 2011 10:52

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