Heterobimetallic Re–Pd, Re–Au and Re–Cu complexes derived from diphenylphosphino cyrhetrene: Synthesis and X-ray structure

Sierra, Diego; Muñoz, Andrés Moreira; Godoy, Fernando; Klahn, A. Hugo; Ibáñez, Andrés; Garland, Marı́a Teresa; Fuentealba, Mauricio

doi:10.1016/j.poly.2008.10.038

Cited by 8 publications

(5 citation statements)

References 29 publications

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“…All chemicals were reagent-grade and used as received unless otherwise specified styrene, p-CH 3 3 ]PdCl 2 (NCMe) complex was prepared according to method reported by our laboratory. 22 GC analyses were performed on an Agilent Technlogies 6890N chromatographer with a flame ionization detector (FID) equipped with a 30 m x 320 µm x 0.25 µm HP-5 column.…”

Section: -Experimental Sectionmentioning

confidence: 99%

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Zúñiga¹,

Sierra

Oyarzo

et al. 2012

J. Chil. Chem. Soc.

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The palladium-catalyzed methoxycarbonylation of vinylarenes has been investigated for the first time using phosphinocyrhetrene [(η 5 -C 5 H 4 PPh 2 )Re(CO) 3 ] a non-metallocenic organometallic ligand. The catalytic system trans- [(η 5 -C 5 H 4 PPh 2 )Re(CO) 3 ]PdCl 2 (NCMe)/PPh 3 (1:2 ratio), carbon monoxide and methanol, in the presence of HCl as acidic promoter, showed good catalytic activity, excellent regioselectivity to the branched products and chemoselectivity up to 94%.Keywords: Methoxycarbonylation, phosphinocyrhetrene ligand, vinylarenes. 1.-INTRODUCTIONPalladium-catalyzed hydroesterification reaction (Reppe carbonylation) is a powerful synthetic strategy for the preparation of linear and branched esters from easily available unsaturated substrates.1,2 It has been established that the regioselectivity of carboxylation products is strongly dependent on the ligands bound to a transition metal and the reaction conditions. The most common catalytic system involve Pd(II) and mono-and bidentate aromatic phosphines. Catalysts containing bidentate diphosphine ligands have been more frequently used for this reaction, but they have the disadvantage to produce branched product in low regio-and enantioselectivity, although a few successful examples have been reported recently.3-7 Several chelating diphosphines have been extensively studied, particularly interesting are those containing metallocenic fragments, for instance, palladium(II) complexes with 1,1-bis(diphenylphosphino)ferrocene (dppf), 1,1-bis(diphenylphosphino) octamethylferrocene (dppomf), 1,1-bis(diphenyl-phosphino)ruthenocene (dppr), and bis(diphenylphosphino)osmocene (dppo) have proven to catalyze the methoxycarbonylation of ethylene and styrene, showing high selectivity to the linear ester. [8][9][10][11][12][13] Gusev et. al.14 have stated that the steric and electronic properties of these metallocenes carrying phosphine ligands, should form M-Pd (M=Fe, Ru and Os) bonds throughout the catalytic cycle, favoring the formation of the linear product. Recently, it has been established, that products with high linearity can be achieved by using chelating systems, in which the diphosphines promote the most favored cis-coordinated complexes. 15On the other hand, palladium complexes containing monodentate phosphine ligands have also been of interest for the catalyzed-hydroesterification reactions since their use provides high regioselectivity to the branched ester but the enantioselectivity is usually low. Despite the large number of monophosphine containing ferrocene described in literature 16 only few of them have been used in hydroesterification reactions. This situation contrast with the remarkably success of ferrocenyl phosphines for palladium catalyzed C-C, C-N and C-O bond-forming cross coupling. 2.-EXPERIMENTAL SECTIONAll experiments were performed under nitrogen using standard Schlenck techniques. Organic solvents were purified by standard methods. All chemicals were reagent-grade and used as received unless otherwise specified styrene...

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Section: -Experimental Sectionmentioning

confidence: 99%

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Zúñiga¹,

Sierra

Oyarzo

et al. 2012

J. Chil. Chem. Soc.

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“…plane was found in the closely related complex (CO) 3 Re(h 5 -C 5 H 4 PPh 2 )PdCl 2 (NCMe), which does not have a bonding interaction between the rhenium and palladium atoms. 10 The short distance between the metal centers also exerts a shortening of the Pd-P bond ( 2 2.3328(10) A ˚). 28 Significant variations from the ideal square-planar geometry are also observed around the Pd center.…”

Section: X-ray Structure Of 3•2ch 3 Cn and 4•ch 2 CLmentioning

confidence: 99%

“…Very recently, we reported the coordination capability to Pd(II), Au(I) and Cu(I) of the ligand (h 5 -C 5 H 4 PPh 2 )Re(CO) 3 supported by crystallographic information. 10 With regard to bidentate ligands, most of the literature reports deal with the anionic derivatives having diphenylphosphinocyclopentadienyl bound to the tricarbonyl moiety of group 6 transition metals, especially molybdenum and tungsten [(h 5 -C 5 H 4 PPh 2 )M(CO) 3 ] -, (M = Mo, W). 11 These anions can be viewed as difunctional chelated ligands, with phosphine and metal anion a Instituto de Química, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.…”

Section: Introductionmentioning

confidence: 99%

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Heterobimetallic RePd complexes bridged by η1:η5-Ph2PC5H4 ligand. Synthesis, electronic and crystal structure of (CO)2(PR3)(η5-C5H4PPh2)Re–PdCl2, R = Me and OMe

et al. 2010

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The new rhenium complexes (eta(5)-C(5)H(4)PPh(2))Re(CO)(2)(PR(3)) (R = Me (1) and OMe (2)) were prepared photochemically from (eta(5)-C(5)H(4)PPh(2))Re(CO)(3) in the presence of PMe(3) or P(OMe)(3). Further reaction of these ligands with PdCl(2)(NCPh)(2) in chloroform, produces the heterobimetallic complexes (CO)(2)(PMe(3))(eta(5)-C(5)H(4)PPh(2))Re-PdCl(2) (3) and (CO)(2)(P(OMe)(3))(eta(5)-C(5)H(4)PPh(2))Re-PdCl(2) (4). IR spectroscopy reveals that both complexes possess a Re-Pd interaction which was confirmed by X-ray crystallography (Re-Pd bond distance = 2.762 A in and 2.774 A in ). Relativistic functional density theory calculations have also been carried out in order to probe the bonding in these compounds.

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“…These results have motivated us to carry on the study of three complexes of palladium (II), derived from cyrhetrenylphosphine ligands [7,8], as precatalysts for the Suzuki cross-coupling of aryl bromides (Fig. 1).…”

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confidence: 99%

Suzuki cross-coupling of aryl bromides catalyzed by cyrhetrenylphosphine complexes of palladium (II)

Sierra

Zúñiga

Buono-Core

et al. 2011

Inorganic Chemistry Communications

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Heterobimetallic Re–Pd, Re–Au and Re–Cu complexes derived from diphenylphosphino cyrhetrene: Synthesis and X-ray structure

Cited by 8 publications

References 29 publications

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Methoxycarbonylation of Styrene by Palladium(ii) Complex Containing the Diphenylphosphinocyrhetrene Ligand

Heterobimetallic RePd complexes bridged by η1:η5-Ph2PC5H4 ligand. Synthesis, electronic and crystal structure of (CO)2(PR3)(η5-C5H4PPh2)Re–PdCl2, R = Me and OMe

Suzuki cross-coupling of aryl bromides catalyzed by cyrhetrenylphosphine complexes of palladium (II)

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