New Pd(<scp>ii</scp>) complexes of sulfur ylides; synthesis, X-ray characterization, a theoretical study and catalytic activity toward the Mizoroki–Heck reaction

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

doi:10.1039/c6ra01390b

Cited by 30 publications

(15 citation statements)

References 48 publications

(52 reference statements)

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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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“…Various reactions for forming a C–C bond are currently under study because of their significant applications . Among them, the Mizoroki–Heck reaction is, perhaps, the most strategic process for the arylation of olefins through palladium‐catalyzed C–C formation reactions .…”

Section: Introductionmentioning

confidence: 99%

Catalytic and antibacterial properties of 3‐dentate carboxamide Pd/Pt complexes obtained via a benign route

Kiani

Bagherzadeh

Meghdadi

et al. 2020

Applied Organom Chemis

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The complexes PdII(qcq)(OAc) and PtII(qcq)Cl have been synthesized using environmentally benign synthesized ligands and characterized by elemental analyses: Fourier transform infrared spectroscopy, UV–visible spectroscopy, 1H NMR spectroscopy, and X‐ray diffraction. The catalytic activity of the complex was assessed, in different media, for the Mizoroki–Heck coupling reaction for typical aryl halides and terminal olefins under aerobic conditions. Since the base and the solvent were found to influence the efficiency of the reaction, reaction conditions, temperature, time, and the amount of K3PO4 and a mixture of H2O/PEG, were optimized. We found, for the Mizoroki–Heck reaction coupling less reactive aryl chloride derivatives with olefins, promising activity for palladium catalysts. The electrochemical behavior of Hqcq and the Pd(II) complex was investigated by cyclic voltammetry and irreversible PdII/I reductions were observed. Hqcq and the Pd(II) and Pt(II) complexes were also screened for their in vitro antibacterial activity. They showed promising antibacterial activity comparable to that of the antibiotic penicillin.

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New Pd(ii) complexes of sulfur ylides; synthesis, X-ray characterization, a theoretical study and catalytic activity toward the Mizoroki–Heck reaction

Abstract: The reaction of sulfur ylides SMe2C(H)C(O)R (R = 4-nitrophenyl, phenyl, and 3-nitrophenyl) with [PdCl2(cod)] gives the new Pd(ii) complexes of type cis- and trans-[PdCl2(SMe2C(H)C(O)R)2] (R = phenyl (1), 3-nitrophenyl (2), and 4-nitrophenyl (3)).

Cited by 30 publications

References 48 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

Catalytic and antibacterial properties of 3‐dentate carboxamide Pd/Pt complexes obtained via a benign route

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