Pyrene Carboxylate Ligand Based Coordination Polymers for Microwave-Assisted Solvent-Free Cyanosilylation of Aldehydes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. Thermogravimetric Analyses
2.3. Crystal Structure Analysis
2.4. Catalytic Activity Studies
3. Materials and Methods
3.1. Synthesis of 5-{(pyren-4-ylmethyl)amino}isophthalic Acid (H2L)
3.2. Synthesis of the Coordination Polymer [Zn(L)(H2O)2]n·n(H2O) (1)
3.3. Synthesis of the Coordination Polymer [Cd(L)(H2O)]n·n(H2O) (2)
3.4. Procedure for the Cyanosilylation Reaction of Aldehydes
3.5. Crystal Structure Determinations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Catalyst | Temperature (°C) | Catalyst Amount (mol%) | Solvent | Yield b (%) |
---|---|---|---|---|---|
1 | 1 | 50 | 2.0 | Solvent free | 97 |
2 | 2 | 50 | 2.0 | Solvent free | 85 |
3 | 1 | 50 | 2.0 | MeOH | 78 |
4 | 1 | 50 | 2.0 | CHCl3 | 67 |
5 | 1 | 50 | 2.0 | CH3CN | 57 |
6 | 1 | 50 | 2.0 | THF | 81 |
7 | 2 | 50 | 2.0 | MeOH | 55 |
8 | 2 | 50 | 2.0 | CHCl3 | 43 |
9 | 2 | 50 | 2.0 | CH3CN | 41 |
10 | 2 | 50 | 2.0 | THF | 76 |
11 | 1 | 50 | 1.0 | Solvent free | 52 |
12 | 1 | 50 | 5.0 | Solvent free | 98 |
13 | 2 | 50 | 1.0 | Solvent free | 30 |
14 | 2 | 50 | 5.0 | Solvent free | 85 |
15 | 1 | 25 | 2.0 | Solvent free | 32 |
16 | 1 | 40 | 2.0 | Solvent free | 81 |
17 | 1 | 60 | 2.0 | Solvent free | 96 |
18 | 2 | 25 | 2.0 | Solvent free | 25 |
19 | 2 | 40 | 2.0 | Solvent free | 80 |
20 | 2 | 60 | 2.0 | Solvent free | 84 |
21 | Blank | 50 | - | Solvent free | 10 |
22 | H2L | 50 | 2.0 | Solvent free | 18 |
23 | Zn(NO3)3·6H2O | 50 | 2.0 | Solvent free | 28 |
24 | Cd(NO3)3·4H2O | 50 | 2.0 | Solvent free | 23 |
Entry | Reactant | Yield b (%) with 1 | Yield b (%) with 2 |
---|---|---|---|
1 | 4-Nitrobenzaldehyde | >99 | 96 |
2 | 3-Nitrobenzaldehyde | 98 | 95 |
3 | 4-Bromobenzaldehyde | >99 | 94 |
4 | 4-Chlorobenzaldehyde | 95 | 89 |
5 | 4-Hydroxybenzaldehyde | 91 | 75 |
6 | 3-Hydroxybenzaldehyde | 88 | 67 |
7 | 4-Methoxybenzaldehyde | 75 | 64 |
8 | 4-Methylbenzaldehyde | 71 | 58 |
Entry | Catalyst | Solvent/Temp/Time | Aldehyde | Yield (%) | Reference |
---|---|---|---|---|---|
1 | 1 | Solvent free/50 °C/1.5 h | Benzaldehyde | 97 | This work |
2 | [Pr(3,5-DSB)(Phen)]n | Solvent free/50 °C/3 h | Benzaldehyde | 78 | [23] |
3 | [{Co0.6Ni1.4(H2O)2(Bpe)2}(V4O12)]·4H2O·Bpe | Solvent free/50 °C/16 h | Benzaldehyde | 77 | [24] |
4 | [NaCu(2,4-HPdc)(2,4-Pdc)] | Solvent free/50 °C/24 h | Benzaldehyde | 85 | [25] |
5 | [Sn(L1)2] | Solvent free/50 °C/4 h | Benzaldehyde | 75 | [26] |
6 | 1 | THF/50 °C/1.5 h | Benzaldehyde | 81 | This work |
7 | [Pb(L1)2]2 | DCM/50 °C/6 h | Benzaldehyde | 97 | [27] |
8 | [Cu3(benzenetricarboxylate)2]n | pentane/40 °C/72 h | Benzaldehyde | 57 | [28] |
9 | [Cd2(1,4-NDC)2(DMF)2]n | Tolene/50 °C/72 h | 4-Nitrobenzaldehyde | 49 | [29] |
10 | {[Zn(dpe)(μ-OOCCH3)2](H2O)}n | DCM/RT/24 h | Benzaldehyde | 14 | [30] |
11 | {[Zn3(4,4′-bpy)4(μ-O2CCH2CH3)4](ClO4)2(4,4′-bpy)2(H2O)4}n | DCM/RT/24 h | Benzaldehyde | 22 | [31] |
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Karmakar, A.; Paul, A.; Sabatini, E.P.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L. Pyrene Carboxylate Ligand Based Coordination Polymers for Microwave-Assisted Solvent-Free Cyanosilylation of Aldehydes. Molecules 2021, 26, 1101. https://doi.org/10.3390/molecules26041101
Karmakar A, Paul A, Sabatini EP, Guedes da Silva MFC, Pombeiro AJL. Pyrene Carboxylate Ligand Based Coordination Polymers for Microwave-Assisted Solvent-Free Cyanosilylation of Aldehydes. Molecules. 2021; 26(4):1101. https://doi.org/10.3390/molecules26041101
Chicago/Turabian StyleKarmakar, Anirban, Anup Paul, Elia Pantanetti Sabatini, M. Fátima C. Guedes da Silva, and Armando J. L. Pombeiro. 2021. "Pyrene Carboxylate Ligand Based Coordination Polymers for Microwave-Assisted Solvent-Free Cyanosilylation of Aldehydes" Molecules 26, no. 4: 1101. https://doi.org/10.3390/molecules26041101