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

Sabounchei, Seyyed Javad; Yousefi, Abed; Ahmadianpoor, M.; Hashemi, Ali; Bayat, Mehdi; Sedghi, Asieh; Bagherjeri, Fateme Akhlaghi; Gable, Robert W.

doi:10.1016/j.poly.2016.05.046

Cited by 25 publications

(6 citation statements)

References 49 publications

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“…The geometries of the aforementioned Pt(II) complexes were fully optimized at BP86/def2‐SVP level of theory. It has been shown that BP86 is a suitable level for calculation of bonding situation between the M ← L in such as these complexes . All calculations were performed using the Gaussian 09 set of programs .…”

Section: Methodssupporting

confidence: 92%

Pallada‐ and platinacycle complexes of phosphorus ylides; synthesis, X‐ray characterization, theoretical and electrochemical studies and application of Pd(II) complexes as catalyst in Suzuki‐Miyaura coupling reaction

Sabounchei

Sedghi

Hashemi

et al. 2017

Applied Organom Chemis

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The new unsymmetrical phosphonium salts [Ph 2 PCH 2 PPh 2 CH 2 C(O)C 6 H 4 R]Br (R= m-Br (S 1 ) and p-CN (S 2 )) were synthesized in the reaction of 1,1bis(diphenylphosphino)methane (dppm) and BrCH 2 C(O)C 6 H 4 R (R= m-Br and p-CN) ketones, respectively. Further treatment with NEt 3 gave the α-keto stabilized phosphorus ylides Ph 2 PCH 2 PPh 2 C(H)C(O)C 6 H 4 R (R= m-Br (Y 1 ) and p-CN (Y 2 )). These ligands were reacted with [MCl 2 (cod)] (M= Pd and Pt; cod= 1,5cyclooctadiene) to give the pallada-and platinacycle complexes [MCl 2 (Ph 2 PCH 2 PPh 2 C(H)C(O)C 6 H 4 R)] (M= Pd, R= m-Br (3); R= p-CN (4) and M= Pt, R= m-Br (5); R= p-CN (6)). Cyclic voltammetry, elemental analysis, IR and NMR ( 1 H, 13 C and 31 P) spectroscopic methods were used for characterization of the obtained compounds. Further, the structure of complexes 3 and 4 were characterized crystallographically. Palladacycles 3 and 4 were proved to be excellent catalysts for the Suzuki-Miyaura coupling reactions of various aryl chlorides and arylboronic acids in mixed DMF/H 2 O media. Also, the bonding situations between two interacted fragments [PtCl 2 ] and Y 1 and Y 2 ligands in platinacycles 5 and 6 were investigated based on DFT method by using NBO, EDA and ETS-NOCV analysis.

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Section: Methodssupporting

confidence: 92%

Pallada‐ and platinacycle complexes of phosphorus ylides; synthesis, X‐ray characterization, theoretical and electrochemical studies and application of Pd(II) complexes as catalyst in Suzuki‐Miyaura coupling reaction

Sabounchei

Sedghi

Hashemi

et al. 2017

Applied Organom Chemis

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“…It has been shown that BP86 is a suitable level for the calculation of the bonding situation between the M ← L in complexes such as these [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50]. Vibrational frequency analyses, done at the same level of theory, indicated that the optimized structures are at the stationary points corresponding to the local minima without any imaginary frequency.…”

Section: Computational Details (Theoretical Studies)mentioning

confidence: 99%

New complexes of Ni(II) and Cu(II) with tridentate ONO Schiff base ligand: synthesis, crystal structures, electrochemical and theoretical investigation

et al. 2018

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In this research, we prepared a new series of the Cu(II) (1) and Ni(II) (2) metal complexes of a tridentate Schiff base ligand, (E)-2-(5-bromo-2-hydroxybenzylideneamino) phenol (H 2 L). These complexes were characterized by elemental analysis, FT-IR, UV-Vis, and 1 H-NMR spectroscopy. The crystal structures of (1) and (2) were determined by X-ray diffraction studies. The single crystal X-ray diffraction analyses revealed that copper(II) cation is five-coordinated and the coordination polyhedron is a slightly distorted square pyramid. Nickel(II), on the other hand, is four-coordinated, and has a regular, square planar geometry. Further discussed were the electrochemical reduction of these complexes. We also analyzed the nature of the metal-ligand bond in the complexes through NBO and EDA analysis. Besides, vibrational sample magnetometer (VSM) revealed complex (1) was ferromagnetic.

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“…Morokuma and Ziegler and Rauk developed EDA in the 1970s. Using this technique, a quantitative computational pattern is in hand for the explanation of the strength of M ← L σ donation, and M → L back‐bonding in main group and transition metal complexes with different types of ligands …”

Section: Resultsmentioning

confidence: 99%

“…All calculations were performed using the Gaussian 09 set of programs . It has been shown in former studies that BP86 is a suitable level for calculation of the bonding situation of M ← L in such as these complexes . For bonding analyses, the terms of EDA were carried out at BP86/TZ2P(ZORA)//BP86/def2‐SVP with C1 symmetry.…”

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

Cited by 25 publications

References 49 publications

Pallada‐ and platinacycle complexes of phosphorus ylides; synthesis, X‐ray characterization, theoretical and electrochemical studies and application of Pd(II) complexes as catalyst in Suzuki‐Miyaura coupling reaction

Pallada‐ and platinacycle complexes of phosphorus ylides; synthesis, X‐ray characterization, theoretical and electrochemical studies and application of Pd(II) complexes as catalyst in Suzuki‐Miyaura coupling reaction

New complexes of Ni(II) and Cu(II) with tridentate ONO Schiff base ligand: synthesis, crystal structures, electrochemical and theoretical investigation

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

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