Five-Membered Cyclic Carbonates: Versatility for Applications in Organic Synthesis, Pharmaceutical, and Materials Sciences
Abstract
:1. Introduction
2. Applications in Chemistry
2.1. Decarboxylation of Cyclic Carbonates
2.2. Hydrogenation Reaction
2.3. Transesterification of Cyclic Carbonates
2.4. Substitution Reaction
2.5. Metal-Catalyzed Miscellaneous Reactions
2.6. Other Reactions
2.7. Alkene Polymerization
2.8. Ring-Opening Polymerization
3. Potential Applications in Biological Studies
3.1. Raw Material Derivatives
3.2. Heterocyclic Compounds
3.3. Bioactive Urethanes and Derivatives
3.4. Other Compounds with Biological Activity
4. Precursors to Materials
4.1. Urethanes and Polyurethanes
4.2. Flame Retardants
4.3. Energy and Electronics
4.4. Non-Ionic Surfactants
- −
- GC 1a and the acid 61 firstly react under acid catalysis to give the GC carboxylate 1q; this intermediate is subsequently decarbonylated to form two isomeric monoglycerides, 12 and 173, which can further undergo stepwise esterification to provide diglycerides 173′ and 174″ and the triglyceride 174 (Scheme 81, route I);
- −
- Firstly, 1a undergoes hydrolysis to glycerol, which similarly reacts with 58 to yield monoglycerides 174 and 12, diglycerides 173′ and 173″, and triglyceride 174 (Scheme 81, route II).
4.5. Miscellaneous
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Condition | R | Product | Yield (%) |
1 | B2pin2 22 (1.2 equivalent) CuCl (9 mol%)/ L1 (13 mol%), Cs2CO3 (15 mol%), CH3OH, r.t., 16 h | aryl | 33–65 | |
2 | Bpin(CH2)Bpin 23, (1.2 equivalent) CuCl (9 mol%), Cs2CO3 (50 mol%), CH3OH, r.t., 16 h | aryl, heteroaryl, vinyl | 48–82 | |
3 | B2pin2 22 (1.2 equivalent) CuCl (9 mol%)/ L2 (13 mol%), Cs2CO3 (15 mol%), CH3OH, r.t., 16 h | alkyl, aryl, heteroaryl | 37–55 | |
4 | Pd2(dba)3.CHCl3 (2.5 mol%) C6H5B(OH)2 24 (20 mol%), (R)-L3 (10 mol%), THF H2O (10 equivalent), 16 h, 40 °C | aryl, heteroaryl | 82–98% (80–98% ee) | |
5 | Pd2(dba)3.CHCl3 (2.5 mol%) B(C2H5)3 25 (10 mol%), (S,S,S)-L4 (10 mol%), THF H2O (10 equivalent), 24 h, 20 °C | alkyl, benzyl, heteroalkyl | 61–87% (80–98% ee) | |
6 | R1OH 7, Pd2(dba)3.CHCl3 (2.5 mol%), B(C2H5)3 25 (5 mol%), (R)-L3 (10 mol%), 40 °C toluene, 4Å MS, 16 h | R = alkyl, aryl, heteroaryl, heteroalkyl R1 = alkyl, benzyl, heteroalkyl, allyl | 56–97% (37–99% ee) |
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Rollin, P.; Soares, L.K.; Barcellos, A.M.; Araujo, D.R.; Lenardão, E.J.; Jacob, R.G.; Perin, G. Five-Membered Cyclic Carbonates: Versatility for Applications in Organic Synthesis, Pharmaceutical, and Materials Sciences. Appl. Sci. 2021, 11, 5024. https://doi.org/10.3390/app11115024
Rollin P, Soares LK, Barcellos AM, Araujo DR, Lenardão EJ, Jacob RG, Perin G. Five-Membered Cyclic Carbonates: Versatility for Applications in Organic Synthesis, Pharmaceutical, and Materials Sciences. Applied Sciences. 2021; 11(11):5024. https://doi.org/10.3390/app11115024
Chicago/Turabian StyleRollin, Patrick, Liane K. Soares, Angelita M. Barcellos, Daniela R. Araujo, Eder J. Lenardão, Raquel G. Jacob, and Gelson Perin. 2021. "Five-Membered Cyclic Carbonates: Versatility for Applications in Organic Synthesis, Pharmaceutical, and Materials Sciences" Applied Sciences 11, no. 11: 5024. https://doi.org/10.3390/app11115024