Synthesis and structural chemistry of CoII, CuII, CuI and PdII complexes containing a flexible monoselenoether ligand

Cargnelutti, Roberta; Delgado, Cássia Pereira; Cervo, Rodrigo; Tirloni, Bárbara; Burrow, Robert A.; Lang, Ernesto Schulz

doi:10.1039/c8nj03621g

Cited by 11 publications

(3 citation statements)

References 35 publications

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“…In the past few decades, organic compounds containing selenium have attracted remarkable concern because of numerous uses in the synthesis of organic and natural products, , pharmacological properties, , biochemistry, catalytic activity, , and synthesis of conducting and semiconducting materials . Also, a series of unique features of these compounds such as the potency of strong electron donating of selenium, stability against moisture and air, and solubility in diverse solvents have led to the preparation of diverse metal complexes of organoselenium ligands. − The promising catalytic activity of these complexes has been displayed in different organic chemical transformations including carbon–carbon coupling reactions, direct boronation of allyl alcohols, oxidation of alcohols, transfer hydrogenation of ketones, and coupling of allyl alcohols and aldehydes …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A³ Coupling Reaction

Rangraz

Nemati

2019

Ind. Eng. Chem. Res.

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In the present work, a novel heterogeneous catalytic system involving copper(I) complex of moisture- and air-stable organoselenium ligand supported on Fe3O4 nanoparticles modified by SiO2/aminopropyltrieethoxysilane was designed, synthesized, and characterized using various physicochemical methods inclusive Fourier transform infrared spectroscopy, X-ray diffraction, vibrating sample magnetometry, field emission scanning electron microscopy, energy dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy, atomic absorption spectroscopy, inductively coupled plasma optical emission spectroscopy, and thermogravimetry. The catalytic activity of the synthesized magnetic nanocatalyst which was named Fe3O4@SiO2-Se-T/CuI was evaluated in A3 coupling reactions for the preparation of propargylamine compounds using diverse aldehydes, secondary amines, and terminal alkynes. The benign reaction condition, variety of substrate scope, good yield, low reaction time, high stability, utilization of organoselenium compound as an air- and moisture-insensitive ligand and its immobilization on solid support, and, more importantly, effortless recovery and recyclability of the catalyst up to five consecutive cycles without remarkable loss in its activity are some of the interesting features of this protocol that makes it more beneficial from both industrial and environmental points of view.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A³ Coupling Reaction

Rangraz

Nemati

2019

Ind. Eng. Chem. Res.

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“…The cif file of 1 obtained by us is available upon request). The structure of 1 was firstly reported by Takenaka et al., [13r] followed by a number of reports of the same structure with variable quality [13a–q,s–x] . The structure of 2 was reported four times [14] .…”

Section: Resultsmentioning

confidence: 99%

EPR, Magnetic, and Computational Characterization of Linear and Zigzag Ladder‐type Chains of Exchange Coupled Cu(II) Complexes with Picolinic and Dipicolinic Acid Ligands

et al. 2021

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We report magnetic, EPR, and computational studies on two representative examples of structurally well‐characterized one dimension (1D) molecular systems: the copper complexes catena‐[bis(μ‐pyridine‐2‐carboxylato)‐copper dihydrate] and catena‐[(μ2‐pyridine‐2,6‐dicarboxylato)‐diaqua‐copper(II)], hereafter 1 and 2, respectively. Experimental and theoretical results confirmed that the structural chains in both compounds behave as magnetic chains in which the copper ions are weakly coupled by isotropic exchange. Magnetic susceptibility measurements of 1 suggested that the copper ions are antiferromagnetically coupled whereas EPR measurements suggested ferromagnetic coupling at temperature above 100 K which becomes antiferromagnetic at low temperatures. Computational calculations would indicate that the ferromagnetic‐antiferromagnetic change may be due to dCu−Oap shortening on lowering temperature temperature (a fact that was observed experimentally by XRD at low temperatures), which redistributes the small Cu(II) unpaired spin density delocalized on the apical ligand to copper. The 1D magnetic behavior of the zigzag ladder chain of 2 is less detectable than that of the single chain of 1. Magnetic susceptibility measurements in conjunction with computational calculations showed that the pathways that give rise to the 1D ladder transmit ferromagnetic exchange interactions with different strengths, with the stronger interaction being transmitted along the rungs. The role of the weaker exchange interactions transmitted along the rails on the magnetic dimensionality of 2 is analyzed.

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“…[15][16][17][18][19][20] They have been termed as Janus element owing to their both nucleophilic and electrophilic characteristics. [20][21][22][23][24][25] Thereby, organoselenium compounds have become quite an attraction amongst the researchers when it comes to organic chemistry, [26,27] alongside their impact in the field of medicinal chemistry, [28,29] material chemistry, [30] chemical biology [31,32] and biochemistry. [33]…”

Section: Introductionmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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Synthesis and structural chemistry of Co^II, Cu^II, Cu^I and Pd^II complexes containing a flexible monoselenoether ligand

Abstract: A monoselenoether ligand (PySeCH2Py) reacts with CoII, CuII, CuI and PdII resulting in the formation of molecular, polymeric or cyclometallated complexes depending on the starting material used and the reaction conditions applied.

Cited by 11 publications

References 35 publications

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A³ Coupling Reaction

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A³ Coupling Reaction

EPR, Magnetic, and Computational Characterization of Linear and Zigzag Ladder‐type Chains of Exchange Coupled Cu(II) Complexes with Picolinic and Dipicolinic Acid Ligands

Insights into the Recent Synthetic Advances of Organoselenium Compounds

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Synthesis and structural chemistry of CoII, CuII, CuI and PdII complexes containing a flexible monoselenoether ligand

Abstract: A monoselenoether ligand (PySeCH2Py) reacts with CoII, CuII, CuI and PdII resulting in the formation of molecular, polymeric or cyclometallated complexes depending on the starting material used and the reaction conditions applied.

Cited by 11 publications

References 35 publications

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A3 Coupling Reaction

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A3 Coupling Reaction

EPR, Magnetic, and Computational Characterization of Linear and Zigzag Ladder‐type Chains of Exchange Coupled Cu(II) Complexes with Picolinic and Dipicolinic Acid Ligands

Insights into the Recent Synthetic Advances of Organoselenium Compounds

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Synthesis and structural chemistry of Co^II, Cu^II, Cu^I and Pd^II complexes containing a flexible monoselenoether ligand

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A³ Coupling Reaction

Design, Synthesis, and Characterization of a Novel Magnetically Recoverable Copper Nanocatalyst Containing Organoselenium Ligand and Its Application in the A³ Coupling Reaction