3,7-Diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) and derivatives: Coordination chemistry and applications

Mahmoud, Abdallah G.; Silva, M. Fátima C. Guedes da; Pombeiro, Armando J. L.

doi:10.1016/j.ccr.2020.213614

Cited by 15 publications

(16 citation statements)

References 69 publications

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“…120.0 (9) 114.5(2) P1-C3-N4 113.5(2) P1-C1-N1 114.2 (4) The presence of an additional substituent on the phosphorus atom leads to considerable differences in bonding geometry of the crystal structures of DAPTA and its homologs, compounds 1-3. The largest differences in bonding geometry were observed in the bonds that involve the P atom and the adjacent C atoms.…”

Section: Single Crystal X-ray Diffraction Analysismentioning

confidence: 99%

“…However, its coordination properties and applications in catalysis remained unexplored until our group has recently reported the copper {[Cu(μ-CH3COO)2(κO-DAPTA=O)]2} and sodium {[Na(μ-1κOOʹ;2κO-DAPTA=O)(MeOH)]2(BPh4)2} complexes, with the former being catalytically active for alcohol oxidation and nitro-aldol condensation in aqueous media [11]. No other studies of this P-functionalization of DAPTA have been reported [9]. Due to the increasing demands for a larger variety of water-soluble ligands for catalytic applications in aqueous media, we have chosen to investigate the functionalization of DAPTA for this purpose.…”

Section: Introductionmentioning

confidence: 99%

“…For comparative purposes, the study was extended to the well-defined Cu(II) complex [Cu(μ-CH3COO)2(κO-DAPTA=O)]2 (4) [11]. No other studies of this P-functionalization of DAPTA have been reported [9]. Due to the increasing demands for a larger variety of water-soluble ligands for catalytic applications in aqueous media, we have chosen to investigate the functionalization of DAPTA for this purpose.…”

Section: Introductionmentioning

confidence: 99%

“…The di- N -acylated derivative of PTA, 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA; Figure 1 ), has acquired the most significant attention when compared to the other PTA analogues due to its incomparable high solubility in water (7.4 M) [ 8 ]. Several transition metal complexes bearing DAPTA ligands have been synthesized and used in aqueous-phase catalysis [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

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Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

et al. 2020

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The 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) derivatives, viz. the already reported 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane 5-oxide (DAPTA=O, 1), the novel 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-sulfide (DAPTA=S, 2), and 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-selenide (DAPTA=Se, 3), have been synthesized under mild conditions. They are soluble in water and most common organic solvents and have been characterized using 1H and 31P NMR spectroscopy and, for 2 and 3, also by single crystal X-ray diffraction. The effect of O, S, or Se at the phosphorus atom on the structural features of the compounds has been investigated, also through the analyses of Hirshfeld surfaces. The presence of 1–3 enhances the activity of copper for the catalytic azide-alkyne cycloaddition reaction in an aqueous medium. The combination of cheaply available copper (II) acetate and compound 1 has been used as a catalyst for the one-pot and 1,4-regioselective procedure to obtain 1,2,3-triazoles with high yields and according to ‘click rules’.

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Section: Single Crystal X-ray Diffraction Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

et al. 2020

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“…A significant interest has been directed to the application of transition metal complexes based on the neutral, water-soluble and air-stable 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo [3.3.1] nonane (DAPTA) ligand in aqueous medium catalysis [24]. In this context, our group has reported the set of copper(I)-DAPTA complexes [CuBr(κP-DAPTA) 3 ] (1), [CuI(κP-DAPTA) 3 ] (2), [Cu(µ-Br)(κP-DAPTA) 2 ] 2 (3) and [Cu(µ-I)(κP-DAPTA) 2 ] 2 (4) (Scheme 1) that demonstrated to be efficient homogeneous catalysts for the microwave-assisted CuAAC reaction [25].…”

Section: Introductionmentioning

confidence: 99%

The Catalytic Activity of Carbon-Supported Cu(I)-Phosphine Complexes for the Microwave-Assisted Synthesis of 1,2,3-Triazoles

et al. 2021

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A set of Cu(I) complexes with 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo-[3.3.1]nonane (DAPTA) phosphine ligands viz. [CuX(κP-DAPTA)3] (1: X = Br; 2: X = I) and [Cu(μ-X)(κP-DAPTA)2]2 (3: X = Br; 4: X = I) were immobilized on activated carbon (AC) and multi-walled carbon nanotubes (CNT), as well as on these materials after surface functionalization. The immobilized copper(I) complexes have shown favorable catalytic activity for the one-pot, microwave-assisted synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition reaction (CuAAC). The heterogenized systems with a copper loading of only 1.5–1.6% (w/w relative to carbon), established quantitative conversions after 15 min, at 80 °C, using 0.5 mol% of catalyst loading (relative to benzyl bromide). The most efficient supports concerning heterogenization were CNT treated with nitric acid and NaOH, and involving complexes 2 and 4 (in the same order, 2_CNT-ox-Na and 4_CNT-ox-Na). The immobilized catalysts can be recovered and recycled by simple workup and reused up to four consecutive cycles although with loss of activity.

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Thiocoumarin‐based Au(I) Complexes and Au(0) Systems over TiO₂ as Hybrid Photocatalysts for Hydrogen Generation under UV–Vis Light

Agrelo‐Lestón,

Llorca,

Martínez

et al. 2024

Advanced Science

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This work focuses on the photocatalytic production of hydrogen from the photodehydrogenation of ethanol using several gold(I) complexes and gold(0) systems over titanium dioxide (P90 TiO2) as hybrid photocatalysts. The photocatalytic systems are composed of at least one coumarin‐based ligand, which can enhance the photocatalytic activity by its photon‐absorbing capacity due to its chromophore properties. The photocatalytic behavior for hydrogen generation of the studied samples is compared under UV–vis light setting the total gold‐based co‐catalyst loading at 1 wt% onto the TiO2 photocatalysts and when the gold content is maintained at 0.25 wt%. The incorporation of gold co‐catalysts results in an enhancement of hydrogen production up to 2.7 times compared to a conventional Au/TiO2 reference sample. The results show an increase in the total hydrogen production under UV–vis light due to the combined presence of coumarin chromophore, gold‐based co‐catalysts, and gold plasmonic nanoparticles. A deep characterization of the samples from each group is performed by UV–vis spectroscopy, XPS, HRTEM, and HAADF‐STEM, observing the presence of plasmonic gold nanoparticles for sample “AuL1NPs” and the reduction of the gold present in sample “AuL1a,” which explains the highest observed hydrogen production rates of this study.

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3,7-Diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) and derivatives: Coordination chemistry and applications

Cited by 15 publications

References 69 publications

Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

The Catalytic Activity of Carbon-Supported Cu(I)-Phosphine Complexes for the Microwave-Assisted Synthesis of 1,2,3-Triazoles

Thiocoumarin‐based Au(I) Complexes and Au(0) Systems over TiO₂ as Hybrid Photocatalysts for Hydrogen Generation under UV–Vis Light

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3,7-Diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) and derivatives: Coordination chemistry and applications

Cited by 15 publications

References 69 publications

Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

The Catalytic Activity of Carbon-Supported Cu(I)-Phosphine Complexes for the Microwave-Assisted Synthesis of 1,2,3-Triazoles

Thiocoumarin‐based Au(I) Complexes and Au(0) Systems over TiO2 as Hybrid Photocatalysts for Hydrogen Generation under UV–Vis Light

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Product

Resources

About

Thiocoumarin‐based Au(I) Complexes and Au(0) Systems over TiO₂ as Hybrid Photocatalysts for Hydrogen Generation under UV–Vis Light