Four-coordinate Pd(II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction

Sabounchei, Seyyed Javad; Panahimehr, Mohammad; Ahmadi, Mohsen; Nasri, Zahra; Khavasi, Hamid Reza

doi:10.1016/j.jorganchem.2012.10.004

Cited by 39 publications

(22 citation statements)

References 64 publications

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“…The palladium(II) complex was prepared based on the previously published method [27]. The complex was recrystallized by slow evaporation over several days from dimethyl sulfoxide solution.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, palladacycle complexes have been employed in Suzuki reactions, as active and more air-inert catalytic candidates [23][24][25][26]. In this context, we were interested to explore the use of a five-membered chelate ring palladacycle, whose X-ray crystal structure has been reported in our previous work [27], as a catalyst precursor for Suzuki cross-coupling in aqueous environments (Scheme 1). This complex gives a high catalytic activity in the coupling reactions of various aryl halides and aryl boronic acids under aerobic conditions.…”

Section: Introductionmentioning

confidence: 99%

“…The stabilized resonance structure of the parent ylide is lost upon the complex formation; thus, the C(26)-C(27) bond length in the orthopalladated complex [1.505(17) Å ] is significantly longer than the corresponding distance found in distortion from a square-planar environment. An interesting structural feature concerns the crystal packing, where intermolecular interactions are observed.…”

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confidence: 99%

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A palladium–phosphine catalytic system as an active and recycable precatalyst for Suzuki coupling in water

Sabounchei

Hosseinzadeh

Panahimehr

et al. 2015

Transition Met Chem

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The Suzuki-Miyaura reaction of various aryl halides with aryl boronic acids using {[Ph 2 PCH 2 PPh 2-CH=C(O)(C 10 H 7 )]PdCl 2 } as a catalyst has been investigated. The X-ray crystal structure of the catalyst reveals a five-membered chelate ring formed by coordination of the ligand through the phosphine group and the ylidic carbon atom to the metal center. This palladacycle exhibited excellent activities and reusability in the aqueous phase for the Suzuki cross-coupling reactions of arylboronic acids with aryl halides. The proposed protocol featured mild reaction conditions and notable simplicity and efficiency using Cs 2 CO 3 as a base in water. The catalytic system could be reused four times without significant loss of activity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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A palladium–phosphine catalytic system as an active and recycable precatalyst for Suzuki coupling in water

Sabounchei

Hosseinzadeh

Panahimehr

et al. 2015

Transition Met Chem

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“…Recently, the application of some phosphorus and sulfur ylides in such cross-coupling reactions by our group was reported [19][20][21]. Although palladium complexes of phosphorus ylides show high efficiency and moisture/air stability, most of them are expensive and have environmental considerations.…”

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confidence: 99%

A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

et al. 2016

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“…[MBr 2 (cod)] (M = Pd or Pt) complexes were prepared according to previously published procedures . Phosphorus ylides Y 1 and Y 2 were synthesized and characterized previously . Toluene, n ‐hexane and chloroform were used as reagent grade and dried over Na/benzophenone and CaCl 2 successively.…”

Section: Methodsmentioning

confidence: 99%

Spectral, crystallographic, theoretical and antibacterial studies of palladium(II)/platinum(II) complexes with unsymmetric diphosphine ylides

Sabounchei

Badpa

Bayat

et al. 2018

Applied Organom Chemis

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The reaction of α‐keto‐stabilized diphosphine ylides [Ph2P(CH2)nPPh2═C(H)C(O)C6H4‐p‐CN] (n = 1 (Y1); n = 2 (Y2)) with dibromo(1,5‐cyclooctadiene) palladium(II)/platinum(II) complexes, [Pd/PtBr2(cod)], in equimolar ratio gave the new cyclometalated Pd(II) and Pt(II) complexes [Br2Pd(κ2‐Y1)] (1), [Br2Pt(κ2‐Y1)] (2), [Br2Pd(κ2‐Y2)] (3) and [Br2Pt(κ2‐Y2)] (4). These compounds were screened in a search for novel antibacterial agents and characterized successfully using Fourier transfer infrared and NMR (1H, 13C and 31P) spectroscopic methods. Also, the structures of complexes 1 and 2 were characterized using X‐ray crystallography. The results showed that the P,C‐chelated complexes 1 and 2 have structures consisting of five‐membered rings, while 3 and 4 have six‐membered rings, formed by coordination of the ligand through the phosphine group and the ylidic carbon atom to the metal centre. Also, a theoretical study of the structures of complexes 1–4 was conducted at the BP86/def2‐SVP level of theory. The nature of metal–ligand bonds in the complexes was investigated using energy decomposition analyses (EDA) and extended transition state combined with natural orbitals for chemical valence analyses. The results of EDA confirmed that the main portions of ΔEint, about 57–58%, in the complexes are allocated to ΔEelstat.

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Four-coordinate Pd(II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction

Cited by 39 publications

References 64 publications

A palladium–phosphine catalytic system as an active and recycable precatalyst for Suzuki coupling in water

A palladium–phosphine catalytic system as an active and recycable precatalyst for Suzuki coupling in water

A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

Spectral, crystallographic, theoretical and antibacterial studies of palladium(II)/platinum(II) complexes with unsymmetric diphosphine ylides

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