Recent Novel Hybrid Pd–Fe3O4 Nanoparticles as Catalysts for Various C–C Coupling Reactions
Abstract
:1. Introduction
2. Urchin-like FePd–Fe3O4: Nanocomposite Magnets
2.1. Synthesis of Urchin-Like Pd–Fe3O4 and L10-FePd–Fe Nanocomposite Magnets
2.2. Magnetic Properties of L10-FePd–Fe Nanocomposites Magnets
3. Magnetically Recyclable Pd–Fe3O4 Hybrid Nanocatalyst: Application in Mizoroki–Heck Reaction
3.1. Synthesis and Characterization of Pd–Fe3O4 Hybrid Nanocatalyst
3.2. Pd–Fe3O4 Hybrid Nanocatalyst: Application in Mizoroki–Heck Reaction
4. Bifunctional Catalyst of Pd/Fe3O4/C: High content of Nanoparticles
4.1. Melt Infiltration Method
4.1.1. Synthesis of Pd/Fe3O4/Charcoal Catalyst and Suzuki–Miyaura Coupling Reaction
4.1.2. Recycling and Pd Leaching Test
4.2. Stöber Method
4.2.1. Synthesis of Fe3O4@C–Pd Catalyst and Suzuki–Miyaura Coupling Reaction
4.2.2. Catalytic Efficiency of Fe3O4@C–Pd-550 Nanocomposite
5. Hybrid Fe3O4/Pd Catalysts: Impact of Organic Capping Agents
5.1. Immobilization of Pd NPs onto Each Fe3O4 Microsphere
5.2. Suzuki Coupling Reaction Using Pd/Fe3O4 Nanoparticles with Various Capping Agents
6. Flower-Like Pd–Fe3O4 and Pd–Fe3O4 Hybrid Nanocatalyst-Embedded Au Nanoparticles
6.1. Synthesis of Pd–Fe3O4 and Au/Pd–Fe3O4 Nanocomposites
6.2. Flower-Like Pd–Fe3O4: Application in Sonogashira Coupling Reactions
6.3. Pd–Fe3O4 Supported Au Nanocatalyst: Applications for Tandem Synthesis of 2-Phenylindoles
7. Transition Metal Loading Pd–Fe3O4 Heterobimetallic Nanoparticles
7.1. Synthesis of Hybrid Cu-Doped Pd–Fe3O4 Nanocatalyst
7.2. Synthesize Cu2O/Pd–Fe3O4 Nanocatalyst
7.3. Hybrid MnO and CoO/Pd–Fe3O4 Nanocomplexes
7.4. Synthesis of Hybrid Ni–Pd–Fe3O4 Nanocomposites
7.5. Applications of Transition Metal-Loaded Pd–Fe3O4 Heterobimetallic Nanoparticles in Organic Reactions
7.5.1. Tandem Synthesis of 2-Phenylbenzofurans
7.5.2. C–H Arylation of 1-Butyl-4-Nitro-1H-Imidazoles
7.5.3. Synthesis of Alkylboronates from Styrene
7.5.4. Suzuki–Miyaura Coupling Reaction
8. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Entry | Pd added b | Temp (°C) | Time (h) | Yield c (%) |
---|---|---|---|---|
1 | 0.054 | 110 | 3 | 93 |
2 | 0.108 | 110 | 3 | 99 |
3 | 0.162 | 110 | 3 | 99 |
4 | 0.108 | 60 | 3 | 19.8 |
5 | 0.108 | 70 | 3 | 34.5 |
6 | 0.108 | 80 | 3 | 51.3 |
7 | 0.108 | 80 | 6 | 57.1 |
8 | 0.108 | 80 | 24 | 91.2 |
9 | 0.108 | 90 | 3 | 69.2 |
10 | 0.108 | 100 | 3 | 85.4 |
Entry | Catalysts | Temp (°C) | Time (h) | Solvent | Conv. a (%) | Product Time Yield (gproduct gPd−1 h−1) |
---|---|---|---|---|---|---|
1 | Pd/Fe3O4/charcoal | 150 | 30 | Toluene/H2O (4:1) | 59 | 3.62 |
2 | Pd/Fe3O4/charcoal | 100 | 4 | Toluene/H2O (4:1) | 4 | 1.84 |
3 | Pd/Fe3O4/charcoal | 100 | 4 | DMSO/H2O (4:1) | 25 | 12.0 |
4 | Pd/Fe3O4/charcoal | 100 | 4 | THF/H2O (4:1) | 35 | 15.1 |
5 | Pd/Fe3O4/charcoal (Pd 0.5 mol %) | 100 | 4 | DMF/H2O (4:1) | 60 | 55.2 |
6 | Pd/Fe3O4/charcoal | 100 | 2 | DMF/H2O (4:1) | 60 | 55.2 |
7 | Pd/charcoal b | 100 | 4 | DMF/H2O (4:1) | 76 | 35.0 |
8 | Pd/Fe3O4/charcoal | 100 | 4 | DMF/H2O (4:1) | >99 | 36.0 |
9 | Fe3O4/charcoal | 100 | 4 | DMF/H2O (4:1) | No reaction | |
10 | Commercial Pd/charcoal | 100 | 4 | DMF/H2O (4:1) | 31 | 14.3 |
Entry | Aryl Halide | Arylboronic Acid | Product | Yield a (%) | Product Time Yield (gproduct gPd−1 h−1) |
---|---|---|---|---|---|
1 | >99 | 36.2 | |||
2 | >99 | 36.3 | |||
3 | >99 | 36.2 | |||
4 | >99 | 43.1 | |||
5 | 45 | 20.9 | |||
6 | 64 | 37.9 | |||
7 | 48 | 18.9 | |||
8 | 99 | 48.6 | |||
9 | 83 | 35.5 | |||
10 | 90 | 38.5 |
Recycle Run | Temp (°C) | Time (h) | Solvent | Conv. a (%) | Product Yield Time (gproduct gPd−1 h−1) |
---|---|---|---|---|---|
1 | 100 | 4 | DMF/H2O (4:1) | >99 | 46.0 |
2 | 100 | 4 | DMF/H2O (4:1) | >99 | 46.0 |
3 | 100 | 4 | DMF/H2O (4:1) | >99 | 46.0 |
Entry | A | Halogen | Time (h) | Yield (%) |
---|---|---|---|---|
1 | H | Br | 6 | 92.22 |
2 | H | Cl | 12 | 63.74 |
3 | NO2 | Br | 6 | 94.51 |
4 | OCH3 | Br | 6 | 87.12 |
Recycle Run | Capping Agent | Average Size (nm) |
---|---|---|
1 | Na3Cit | 3.3 ± 0.24 |
2 | PEG | 3.4 ± 0.21 |
3 | PVP | 4.1 ± 0.43 |
4 | No capping agent | 4.7 ± 0.35 |
Entry | Cat. (mol %) | Temp (°C) | Time (h) | Base | Solvent | Yield b (%) |
---|---|---|---|---|---|---|
1 | 1 (Na3Cit) | 80 | 5 | K2CO3 | DMF/H2O (4:1) | 91 |
2 | 1 (Na3Cit) | 50 | 5 | K2CO3 | H2O | 97 |
3 | 0.1 (Na3Cit) | 50 | 5 | K2CO3 | H2O | 65 |
4 | 0.05 (Na3Cit) | 50 | 5 | Cs2CO3 | H2O | 89 |
5 | 0.05 (Na3Cit) | 50 | 7 | Cs2CO3 | H2O | 98 |
6 | 0.05 (Na3Cit) | 50 | 5 | CsOH | H2O | 66 |
7 | 0.05 (Na3Cit) | 40 | 12 | Cs2CO3 | H2O | 48 |
8 | 0.05 (Na3Cit) | 40 | 24 | Cs2CO3 | H2O | 94 |
9 | 0.1 (Na3Cit) | 40 | 12 | Cs2CO3 | H2O | 76 |
10 | 0.05 (Na3Cit) | 100 | 1 | Cs2CO3 | H2O | 80 |
11 | 0.05 (Na3Cit) | 100 | 1.5 | Cs2CO3 | H2O | 98 |
12 | 0.05 (Na3Cit) | 25 | 24 | Cs2CO3 | H2O | 13 |
13 | 0.05 (PEG) | 50 | 7 | Cs2CO3 | H2O | 89 |
14 | 0.05 (No) | 50 | 7 | Cs2CO3 | H2O | 57 |
15 | 0.05 (PVP) | 50 | 7 | Cs2CO3 | H2O | 37 |
Entry | Cat. (mol %) | Temp (°C) | Time (h) | Base | Solvent | Conv. (%) a |
---|---|---|---|---|---|---|
1 | 1 | 120 | 18 | Piperidine | DMF | 72 |
2 | 1 | 120 | 18 | Piperidine | NMP | 76 |
3 | 1 | 120 | 18 | Piperidine | DMSO | 99 |
4 | 1 | 120 | 18 | Cs2CO3 | DMSO | 73 |
5 | 1 | 120 | 18 | NaOAc | DMSO | 98 |
6 | 1 | 120 | 18 | K2CO3 | DMSO | 78 |
7 | 1 | 90 | 18 | Piperidine | DMSO | 92 |
8 | 0.5 | 120 | 3 | Piperidine | DMSO | 99 |
9 | 0.25 | 120 | 3 | Piperidine | DMSO | 94 |
10 | 0.5 | 120 | 1 | Piperidine | DMSO | 93 |
Entry | Aryl Halide | Arylacetylene | Product | Conversion (%) a |
---|---|---|---|---|
1 | 72 | |||
2 | 76 | |||
3 | 99 | |||
4 | 73 | |||
5 | 98 | |||
6 | 78 | |||
7 | 92 | |||
8 | 99 | |||
9 | 94 |
Entry | Catalyst | Temp (°C) | Time (h) | Base | Conversion (%) a |
---|---|---|---|---|---|
1 | Pd–Fe3O4 | 120 | 18 | Piperidine | Trace b |
2 | Pd–Fe3O4 | 120 | 18 | Piperidine | 3 c |
3 | Pd–Fe3O4 | 120 | 18 | Piperidine | 41 |
4 | Pd–Fe3O4 | 120 | 18 | LiOAc | 45 |
5 | Pd–Fe3O4 | 120 | 18 | CsOAc | 48 |
6 | Au/Pd–Fe3O4 | 120 | 18 | CsOAc | 57 |
7 | Au/Pd–Fe3O4 | 150 | 18 | CsOAc | 97 |
8 | Au/Pd–Fe3O4 | 150 | 9 | CsOAc | 97 |
9 | Au/Pd–Fe3O4 | 150 | 6 | CsOAc | 59 |
10 | Au/Pd–Fe3O4 | 150 | 9 | CsOAc | 38 d |
SI No | Catalyst | Size (nm) | Morphology | Application |
---|---|---|---|---|
1 | Pd–Fe3O4 | 8.7 | Spherical | Mizoroki–Heck reaction |
2 | Pd–Fe3O4 | 213 | Flower-like | Sonogashira coupling reaction |
3 | Au/Pd–Fe3O4 | 5.8 | Flower-like | Tandem synthesis reaction |
Entry | Catalysts | Time (h) | Temp (°C) | Conv a (%) |
---|---|---|---|---|
1 | Pd–Fe3O4 | 18 | 130 | 62 |
2 | Cu2O/Pd–Fe3O4 | 18 | 130 | 73 |
3 | Cu2O/Pd–Fe3O4 | 18 | 140 | 85 b |
4 | Cu2O/Pd–Fe3O4 | 9 | 140 | 84 b |
5 | Cu2O/Pd–Fe3O4 | 4.5 | 140 | 76 b |
6 | Cu2O/Pd–Fe3O4 | 9 | 140 | 76 b, c |
7 | Pd/charcoal | 4.5 | 140 | 69 b |
8 | Fe3O4/charcoal | 4.5 | 140 | 0 b |
9 | Cu2O | 4.5 | 140 | 0 b |
Entry | Substrate | Conv. (%) | Entry | Substrate | Conv. (%) |
---|---|---|---|---|---|
1 | 84 | 6 | 70 | ||
2 | 79 | 7 | 39 | ||
3 | 84 | 8 | 71 | ||
4 | 85 | 9 | 80 | ||
5 | 75 | 10 | 69 |
Entry | Catalysts | Solvent | Base | Time (h) | Yield (%) a |
---|---|---|---|---|---|
1 | CoO/Pd–Fe3O4 | MeOH | KOtBu | 12 | Trace |
2 | CoO/Pd–Fe3O4 | THF | KOtBu | 12 | 33 |
3 | CoO/Pd–Fe3O4 | THF | NaOMe | 12 | 36 |
4 | CoO/Pd–Fe3O4 | THF | Cs2CO3 | 12 | 67 |
5 | MnO/Pd–Fe3O4 | THF | Cs2CO3 | 12 | 29 |
6 | Pd–Fe3O4 | THF | Cs2CO3 | 12 | 35 |
7 | Pd/charcoal | THF | Cs2CO3 | 12 | Trace |
8 | CoO/Pd–Fe3O4 | THF | Cs2CO3 | 24 | 63 |
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Jang, S.; Hira, S.A.; Annas, D.; Song, S.; Yusuf, M.; Park, J.C.; Park, S.; Park, K.H. Recent Novel Hybrid Pd–Fe3O4 Nanoparticles as Catalysts for Various C–C Coupling Reactions. Processes 2019, 7, 422. https://doi.org/10.3390/pr7070422
Jang S, Hira SA, Annas D, Song S, Yusuf M, Park JC, Park S, Park KH. Recent Novel Hybrid Pd–Fe3O4 Nanoparticles as Catalysts for Various C–C Coupling Reactions. Processes. 2019; 7(7):422. https://doi.org/10.3390/pr7070422
Chicago/Turabian StyleJang, Sanha, Shamim Ahmed Hira, Dicky Annas, Sehwan Song, Mohammad Yusuf, Ji Chan Park, Sungkyun Park, and Kang Hyun Park. 2019. "Recent Novel Hybrid Pd–Fe3O4 Nanoparticles as Catalysts for Various C–C Coupling Reactions" Processes 7, no. 7: 422. https://doi.org/10.3390/pr7070422