Continuous N-alkylation reactions of amino alcohols using γ-Al₂O₃ and supercritical CO₂: unexpected formation of cyclic ureas and urethanes by reaction with CO₂

Scholarly Works

• Alfano, A. I.; García-Lacuna, J.; Griffiths, O. M.; Ley, S. V.; Baumann, M. Continuous flow synthesis enabling reaction discovery. Chemical Science 2024. doi:10.1039/d3sc06808k
• Fujii, R.; Yabushita, M.; Asada, D.; Tamura, M.; Nakagawa, Y.; Takahashi, A.; Nakayama, A.; Tomishige, K. Continuous Flow Synthesis of 2-Imidazolidinone from Ethylenediamine Carbamate in Ethylenediamine Solvent over the CeO2 Catalyst: Insights into Catalysis and Deactivation. ACS Catalysis 2023, 13, 1562–1573. doi:10.1021/acscatal.2c05721
• Liu, S.; Zhao, W.; Tang, Z.; Zhang, L.; Guo, K.; Wang, H.; Men, Y.; Yang, J.; Dai, J. Design of a Nanoscale Ni Catalyst for Debenzylation Reactions via Hydrogenative C–N Bond Cleavage. Catalysis Letters 2022, 153, 3031–3043. doi:10.1007/s10562-022-04196-9
• Chen, Y.; Monbaliu, J. M. doi:10.1002/9783527824595.ch7
• Rodriguez-Zubiri, M.; Felpin, F.-X. Analytical Tools Integrated in Continuous-Flow Reactors: Which One for What?. Organic Process Research & Development 2022, 26, 1766–1793. doi:10.1021/acs.oprd.2c00102
• Matsuo, H.; Choi, J.-C.; Fujitani, T.; Fujita, K.-i. Carbonylation of o-phenylenediamines with CO2 to 2-benzimidazolones catalyzed by alumina. Tetrahedron Letters 2022, 96, 153772. doi:10.1016/j.tetlet.2022.153772
• Ke, J.; Gao, C.; Folgueiras-Amador, A. A.; Jolley, K. E.; de Frutos, O.; Mateos, C.; Rincón, J. A.; Brown, R. C. D.; Poliakoff, M.; George, M. W. Self-Optimization of Continuous Flow Electrochemical Synthesis Using Fourier Transform Infrared Spectroscopy and Gas Chromatography. Applied spectroscopy 2021, 76, 38–50. doi:10.1177/00037028211059848
• Chemistry: Necessary for Sustainable Technology, but Not Sufficient. Chemistry for Sustainable Technologies: A Foundation; The Royal Society of Chemistry, 2021; pp 247–329. doi:10.1039/bk9781788012058-00247
• He, D.; Wang, H.; Shi, F. CO2 as a Building Block in Organic Synthesis; Wiley, 2020; pp 95–153. doi:10.1002/9783527821952.ch4
• Sunil, D.; Kumar, N. V. A. Use of supercritical carbon dioxide in alkylation reactions. Green Sustainable Process for Chemical and Environmental Engineering and Science; Elsevier, 2020; pp 105–131. doi:10.1016/b978-0-12-817388-6.00006-4
• Sagmeister, P.; Williams, J. D.; Hone, C. A.; Kappe, C. O. Laboratory of the future: a modular flow platform with multiple integrated PAT tools for multistep reactions. Reaction Chemistry & Engineering 2019, 4, 1571–1578. doi:10.1039/c9re00087a
• Dalpozzo, R.; Della Ca, N.; Gabriele, B.; Mancuso, R. Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis. Catalysts 2019, 9, 511. doi:10.3390/catal9060511
• Qi, X.; Zhou, R.; Peng, J.-B.; Ying, J.; Wu, X.-F. Selenium‐Catalyzed Carbonylative Synthesis of 2‐Benzimidazolones from 2‐Nitroanilines with TFBen as the CO Source. European Journal of Organic Chemistry 2019, 2019, 5161–5164. doi:10.1002/ejoc.201801739
• Casnati, A.; Motti, E.; Mancuso, R.; Gabriele, B.; Della Ca, N. Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones. Catalysts 2019, 9, 28. doi:10.3390/catal9010028
• Niemi, T.; Repo, T. Antibiotics from Carbon Dioxide: Sustainable Pathways to Pharmaceutically Relevant Cyclic Carbamates. European Journal of Organic Chemistry 2018, 2019, 1180–1188. doi:10.1002/ejoc.201801598
• Yanovsky, V. A.; Andropov, M. O.; Fakhrislamova, R. S.; Churkin, R. A.; Minaev, K. M.; Yanovskaya, E. A. The Effect of Duration of Amidation of Fatty Acids with Diethanolamine on the Surfactant Properties. Journal of Surfactants and Detergents 2018, 22, 641–654. doi:10.1002/jsde.12235
• Wu, L.; Abada, Z.; Lee, D. S.; Poliakoff, M.; George, M. W. Combining engineering and chemistry for the selective continuous production of four different oxygenated compounds by photo-oxidation of cyclopentadiene using liquid and supercritical CO2 as solvents. Tetrahedron 2018, 74, 3107–3112. doi:10.1016/j.tet.2017.11.048
• Niemi, T.; Fernández, I.; Steadman, B.; Mannisto, J. K.; Repo, T. Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols. Chemical communications (Cambridge, England) 2018, 54, 3166–3169. doi:10.1039/c8cc00636a
• Sullivan, R. J.; Newman, S. G. Flow-Assisted Synthesis of Heterocycles at High Temperatures. Topics in Heterocyclic Chemistry; Springer International Publishing, 2018; pp 161–186. doi:10.1007/7081_2018_18
• Meyer, A. G.; Bissember, A. C.; Hyland, C. J.; Williams, C. C.; Szabo, M.; Abel, S.-A. G.; Bird, M. J.; Hyland, I. K.; Pham, H. Seven-Membered Rings. Progress in Heterocyclic Chemistry; Elsevier, 2018; pp 493–550. doi:10.1016/b978-0-08-102788-2.00016-7

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