Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions
Abstract
:1. Introduction
2. Results and Discussion
2.1. CNS-Pd Synthesis and Characterization
2.2. Suzuki–Miyaura Reaction Optimization
2.3. Suzuki–Miyaura Substrate Scope
2.4. Multiple Cross-Coupling Suzuki–Miyaura Reactions
2.5. Leaching Tests
2.6. Recyclability Tests
3. Conclusions
4. Materials and Methods
4.1. TEMPO-Oxidized Cellulose (TOC) Production and Titration and Synthesis of Cellulose NanoSponges (CNS)
4.2. Preparation of the Catalyst
4.3. Catalyst Characterization
4.4. Suzuki–Miyaura Reaction
4.5. Reaction Work-Up and Product Purification
4.6. Leaching Test
4.7. Reusability Test
4.8. NMR Product Characterization
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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Entry | T (°C) | T (h) | Yield (%) |
---|---|---|---|
1 | 25 (RT) | 48 | 19 |
2 | 80 | 0.5 | 57 |
3 | 100 | 0.33 | 72 |
4 | 100 | 0.5 | 92 |
5 b | 100 | 0.5 | 19 |
Entry | CNS-Pd (%) | Pd (%) | Yield (%) |
---|---|---|---|
1 | 0 | 0.00 | 0 |
2 | 2 | 0.45 | 92 |
3 | 5 | 1.14 | 95 |
4 | 10 | 2.27 | 94 |
5 b | 10 | - | 0 |
Entry | Base | Yield (%) |
---|---|---|
1 | - | 15 |
2 | NaOAc | 54 |
3 | Na2CO3 | 25 |
4 | K2CO3 | 25 |
5 | KOH | 92 |
Entry | TBAB Equivalents | Conversion (%) |
---|---|---|
1 | 0.60 | 92 |
2 | 0.30 | 96 |
3 | 0.15 | 97 |
4 | 0 | 90 |
5 b | 0 | 60 |
6 b | 0.15 | 95 |
Entry | ArX | R | R′ | R″ | R‴ | X | Conversion (%) |
---|---|---|---|---|---|---|---|
1 | 1a | -H | -OCH3 | -H | -H | -Br | 99 |
2 | 1b | -H | -H | -OCH3 | -H | -Br | 98 |
3 | 1c | -H | -H | -H | -OCH3 | -Br | 54 |
4 c | 1c | -H | -H | -H | -OCH3 | -Br | 38 |
5 b | 1d | -H | -CH3 | -H | -H | -Br | 72 |
6 b | 1e | -H | -CHO | -H | -H | -Br | 13 |
7 b,c | 1e | -H | -CHO | -H | -H | -Br | 80 |
8 | 1f | -H | -H | -H | -H | -Br | 93 |
9 | 1g | -H | -NH2 | -H | -H | -Br | 76 |
10 | 1h | -CN | -H | -H | -H | -Br | 99 |
11 | 1i | -H | -H | -H | -H | -Cl | 55 |
Entry | Cycle Number | Yield (%) |
---|---|---|
1 | I | 97 |
2 | II | 99 |
3 | III | 98 |
4 | IV | 99 |
5 | V | 96 |
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Riva, L.; Nicastro, G.; Liu, M.; Battocchio, C.; Punta, C.; Sacchetti, A. Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions. Gels 2022, 8, 789. https://doi.org/10.3390/gels8120789
Riva L, Nicastro G, Liu M, Battocchio C, Punta C, Sacchetti A. Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions. Gels. 2022; 8(12):789. https://doi.org/10.3390/gels8120789
Chicago/Turabian StyleRiva, Laura, Gloria Nicastro, Mingchong Liu, Chiara Battocchio, Carlo Punta, and Alessandro Sacchetti. 2022. "Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions" Gels 8, no. 12: 789. https://doi.org/10.3390/gels8120789