Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles

La optimización de reacciones químicas mediante el uso de catalizadores permite reducir los tiempos de reacción e incrementar el rendimiento de estas. Los catalizadores homogéneos de tipo metal-carbeno NHC mesoiónicos, suelen presentar una alta selectividad, una actividad mejorada y mejor estabilida...

Full description

Autores:
Prada Rojas, Lizeth Daniela
Tipo de recurso:
Trabajo de grado de pregrado
Fecha de publicación:
2023
Institución:
Universidad Santo Tomás
Repositorio:
Repositorio Institucional USTA
Idioma:
spa
OAI Identifier:
oai:repository.usta.edu.co:11634/53255
Acceso en línea:
http://hdl.handle.net/11634/53255
Palabra clave:
Catalyst
Methylation
DES
Cobalt-NHC
Carbene
solventes orgánicos
catalizadores
reacciones químicas
reacciones orgánicas
Catalizador
Metilación
DES
Cobalto-NHC
Carbeno
Rights
openAccess
License
Atribución-NoComercial-CompartirIgual 2.5 Colombia
id SANTOTOMAS_33f5fed85804d671fe55157994dd608d
oai_identifier_str oai:repository.usta.edu.co:11634/53255
network_acronym_str SANTOTOMAS
network_name_str Repositorio Institucional USTA
repository_id_str
dc.title.spa.fl_str_mv Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
title Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
spellingShingle Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
Catalyst
Methylation
DES
Cobalt-NHC
Carbene
solventes orgánicos
catalizadores
reacciones químicas
reacciones orgánicas
Catalizador
Metilación
DES
Cobalto-NHC
Carbeno
title_short Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
title_full Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
title_fullStr Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
title_full_unstemmed Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
title_sort Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles
dc.creator.fl_str_mv Prada Rojas, Lizeth Daniela
dc.contributor.advisor.none.fl_str_mv Osorio Martínez, Carlos Alberto
Alvarado Rueda, Lizeth Johanna
dc.contributor.author.none.fl_str_mv Prada Rojas, Lizeth Daniela
dc.subject.keyword.spa.fl_str_mv Catalyst
Methylation
DES
Cobalt-NHC
Carbene
topic Catalyst
Methylation
DES
Cobalt-NHC
Carbene
solventes orgánicos
catalizadores
reacciones químicas
reacciones orgánicas
Catalizador
Metilación
DES
Cobalto-NHC
Carbeno
dc.subject.lemb.spa.fl_str_mv solventes orgánicos
catalizadores
reacciones químicas
reacciones orgánicas
dc.subject.proposal.spa.fl_str_mv Catalizador
Metilación
DES
Cobalto-NHC
Carbeno
description La optimización de reacciones químicas mediante el uso de catalizadores permite reducir los tiempos de reacción e incrementar el rendimiento de estas. Los catalizadores homogéneos de tipo metal-carbeno NHC mesoiónicos, suelen presentar una alta selectividad, una actividad mejorada y mejor estabilidad en comparación con sistemas análogos más clásicos en los que se utilizan ligandos de organofosfina. El principal impacto negativo en la síntesis de catalizadores es la utilización de solventes orgánicos, por lo que se ha propuesto el uso de solventes eutécticos profundos (DES), los cuales suelen estar constituidos por dos o tres compuestos; una sal de amonio cuaternaria complejada con un compuesto donor de hidrogeno o una sal metálica. En este trabajo, se planteó la síntesis de un catalizador de tipo metal-carbeno NHC mesoiónico mediante una serie de reacciones “click chemistry”, metilación y reacciones de acomplejación con un metal de transición por vía tradicional y por vía DES. Los compuestos obtenidos se caracterización mediante infrarrojo, resonancia magnética y puntos de fusión. Y se evaluó la actividad catalítica del metal-carbenoNHC obtenido en reacciones de Biginelli. Estos procesos se compararon en términos de rendimientos de reacción. La complejación del catalizador se vio favorecida por el uso de DES, pese a que en la “Click chemistry” y la metilación el rendimiento fue menor a que por la vía tradicional. Para poder evaluar su actividad catalítica es necesario continuar probando con diferentes reacciones.
publishDate 2023
dc.date.accessioned.none.fl_str_mv 2023-12-18T19:07:04Z
dc.date.available.none.fl_str_mv 2023-12-18T19:07:04Z
dc.date.issued.none.fl_str_mv 2023-12-18
dc.type.local.spa.fl_str_mv Trabajo de grado
dc.type.version.none.fl_str_mv info:eu-repo/semantics/acceptedVersion
dc.type.category.spa.fl_str_mv Formación de Recurso Humano para la Ctel: Trabajo de grado de Pregrado
dc.type.coar.none.fl_str_mv http://purl.org/coar/resource_type/c_7a1f
dc.type.drive.none.fl_str_mv info:eu-repo/semantics/bachelorThesis
format http://purl.org/coar/resource_type/c_7a1f
status_str acceptedVersion
dc.identifier.citation.spa.fl_str_mv Prada Rojas, L.D. (2023). Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles. [Trabajo de pregrado]. Universidad Santo Tomás, Bucaramanga, Colombia.
dc.identifier.uri.none.fl_str_mv http://hdl.handle.net/11634/53255
dc.identifier.reponame.spa.fl_str_mv reponame:Repositorio Institucional Universidad Santo Tomás
dc.identifier.instname.spa.fl_str_mv instname:Universidad Santo Tomás
dc.identifier.repourl.spa.fl_str_mv repourl:https://repository.usta.edu.co
identifier_str_mv Prada Rojas, L.D. (2023). Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles. [Trabajo de pregrado]. Universidad Santo Tomás, Bucaramanga, Colombia.
reponame:Repositorio Institucional Universidad Santo Tomás
instname:Universidad Santo Tomás
repourl:https://repository.usta.edu.co
url http://hdl.handle.net/11634/53255
dc.language.iso.spa.fl_str_mv spa
language spa
dc.relation.references.spa.fl_str_mv Aguilera, E. (2021). Derivados de monastrol a partir de β-cetoésteres lipofilicos por la reacción de Biginelli. Investigación Joven, 8(2), 26-32.
Akter, M., Rupa, K., & Anbasaran, P. (2022). 1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds. Chem. Rev, 122(15), 13108-13205. https://doi.org/10.1021/acs.chemrev.1c00991
Alonso, D., Baeza, A., Chinchilla, R., Gómez, C., Guillena, G., Marset, X., . . . Saavedra, B. (2018). Mezclas eutécticas como alternativa sostenible a los disolventes. An. Quim, 79-87.
Andruch, V., Varvfalvyová, A. H., Jatkowska, N., & Płotka-Wasylka, J. (2022). Application of deep eutectic solvents in bioanalysis. Trends in Analytical. Trends in Analytical Chemistry, 154(116660), 1-19. https://doi.org/10.1016/j.trac.2022.116660
Aravena, C., Lee, D., Park, J., & Yoo, Y. (2022). Characteristics of Deep eutectic solvents for CO2 capture with Hydro effects for improvement of mass transfer. Journal of industrial and engineering chemistry, 111, 337-345. https://doi.org/10.1016/j.jiec.2022.04.015
Arnold, J., Brothers, P., Mountford, P., Piers, W., Thomas, C., & Tilley, T. (2014). The influence of Michael Lappert on the chemistry landscape. Dalton Trans, 43(44), 16533-16556. https://doi.org/10.1039/C4DT90167C
Bellotti, P., Koy, M., & Hopkinson, M. &. (2021). Recent advances in the chemistry and applications of N-heterocyclic carbenes. Nat. Rev. Chem, 5, 711-725. https://doi.org/10.1038/s41570-021-00321-1
Bera, S., & Szotak, M. (2022). Cobalt-N-Heterocyclic carbene complex in catalysis. ACS Catal, 12(5), 3111-3137. https://doi.org/10.1021/acscatal.1c05869
Bharti, R., Verme, M., Thakys, A., & Sharma, R. (2022). N-Heterocyclic Carbenes (NHCs): An Introduction. Varanasi: IntechOpen. https://doi.org/10.5772/intechopen.102760
Bhujabal, Y., Vadagaonkar, K., & Kapdi, A. (2019). Pd/PTABS: catalyst for efficient C-H (hetero) arylation of 1, 3, 4-oxadiazoles using bromo (hetero) arenes. Asian Journal of Organic Chemistry, 8(2), 289-295. https://doi.org/10.1002/ajoc.201800713
Binandeh, M., Nasseri, M., & Allahresani, A. (2022). High-Power and High-Performance Catalyst for Suzuki Coupling Reaction. Catalysts, 12(9), 1-13. https://doi.org/10.3390/catal12090976
Chen, Y., & Mu, T. (2019). Application of deep eutectic solvents in biomass pretreatment and conversion. Green. Energy Environ, 4, 95-115. https://doi.org/10.1016/j.gee.2019.01.012
Chorkendorff, I., & Niemantsverdriet, J. (2017). Concepts of Modern Catalysis and Kinetics. Wiley VCH.
Contreras, R. (2021). Catálisis homogénea con metales de transición: transformando el mundo de la química. Mérida: CDCHTA.
Corrigan, N., Zhernakov, L., Hashim, M., Xu, J., & Boyer, C. (2019). Flow mediated metal free PET-RAFT polymerisation for upscaled and consistent polymer production. Reaction Chemistry & Engineering, 4(7), 1216-1228. https://doi.org/10.1039/C9RE00014C
Crabtree, R. (2013). Abnormal, mesoionic and remote N-heterocyclic carbene complexes. Coordination Chemistry Reviews, 257, 755-766. https://doi.org/10.1016/j.ccr.2012.09.006
Dalko, P. (2013). Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications. Wiley‐VCH. https://doi.org/10.1002/9783527658862
Danopoulos, A., Massard, G., Frison, G., & Braunstein, P. (2018). Iron and Cobalt Metallotropism in Remote-Substituted NHC Ligands: Metalation to Abnormal NHC Complexes or NHC Ring Opening. Angew. Chem. Int. Ed, 57, 14550-14554. https://doi.org/10.1002/anie.201808008
Danopoulos, A., Simler, T., & Braunstein, P. (2019). N-Hetercyclic carbene complexes of copper, nickel and cobalt. Chem. Rev, 119, 3730-3961. https://doi.org/10.1021/acs.chemrev.8b00505
De Fatima, A., Cafiero, T., Silva, B., & Da Silva, L. (2021). Green Synthetic Approaches for Biologically Relevant Heterocycles. Santiniketan: Elsevier. https://doi.org/10.1016/C2018-0-05415-8
De Frémont, P., Marion, N., Nolan, & S. (2009). Carbenes: Synthesis, properties, and organometallic chemistry. Coordin. Chem. Rev, 253, 862-892. https://doi.org/10.1016/j.ccr.2008.05.018
Devaraj, N., & Finn, M. (2021). Introduction: Click Chemistry. Chem. Rev, 121(12), 6697-6698. https://doi.org/10.1021/acs.chemrev.1c00469
Díez‐González, S. (2016). N-heterocyclic carbenes : from laboratory curiosities to efficient synthetic tools. London: The Royal Society of Chemistry. https://doi.org/10.1039/9781782626817
Dongkun, Y., Zhimin, X., & Tiancheng, M. (2022). Deep eutectic solvents as a green toolbox for synthesis. Cell Reports Physical Science, 3(100809), 1-23. https://doi.org/10.1016/j.xcrp.2022.100809
Du, J., Wang, L., & Xie, M. &. (2015). A Two-Coordinate Cobalt(II) Imido Complex with NHC Ligation: Synthesis, Structure, and Reactivity. Angew. Chem. Int. Ed, 54, 12640-12644. https://doi.org/10.1002/anie.201505937
El Achkar, T., Greige Gerges, H., & Fourmentin, S. (2022). Basics and properties of deep eutectic solvents: a review. Basics and properties of deep eutectic solvents: a review, 19(29), 3397-3408. https://doi.org/10.1007/s10311-021-01225-8
EPA. (9 de Mayo de 2023). EPA. EPA.gov: https://www.epa.gov/greenchemistry/basics-green-chemistry#:~:text=Green%20chemistry%20is%20the%20design,%2C%20use%2C%20and%20ultimate%20disposal.
Fürstner, A. (2016). Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion. ACS Cent. Sci, 2(11), 778-789. https://doi.org/10.1021/acscentsci.6b00272
Girard, S., Knauber, T., & Li, C. (2014). The cross-dehydrogenative coupling of C (sp3)- H bonds: a versatile strategy for C-C bond formations. Angew. Chem. Int. Ed., 53(1), 74-100. https://doi.org/10.1002/anie.201304268
Gronert, S., Keeffe, J., & More O'Ferrall, R. (2011). Stabilities of Carbenes: Independent Measures for Singlets and Triplets. J. Am. Chem. Soc, 133(10), 3381-3389. https://doi.org/10.1021/ja1071493
Guo, L., Srimontree, W., Zhu, C., Maity, B., Xiangqian, L., Cavallo, L., & Rueping, M. (2019). Nickel-catalyzed Suzuki–Miyaura cross-couplings of aldehydes. Nature Communications, 10(1957), 1-6. https://doi.org/10.1038/s41467-019-09766-x
Hameury, S., P, D. F., & Braunstein, P. (2017). Metal complexes with oxygen-functionalized NHC ligands: synthesis and applications. Chem. Soc. Rev, 46, 632-733. https://doi.org/10.1039/C6CS00499G
Hammond, O., Bowron, D., & Edler, K. (2017). The Effect of Water upon Deep Eutectic Solvent Nanostructure: An Unusual Transition from Ionic Mixture to Aqueous Solution. Angew. Chem. Int, 56, 9782-9785. https://doi.org/10.1002/anie.201702486
Hansen, B. S., Klein, J., Horton, A., Adhikari, L., Zelovich, T., Doherty, B., & al, e. (2021). Deep eutectic solvents: a review of fundamentals and application. Chem. Rev, 1232-1285. https://doi.org/10.1021/acs.chemrev.0c00385
Hasan, A., & Pandey, L. (2014). Nanobiomaterials: Nanostructured Materials for Biomedical Applications. Guwahati: Elsevier. https://doi.org/10.1016/C2015-0-01648-3
Hering, F., Berthel, J. H., Lubitz, K., Paul, U. S., Schneider, H., Harterich, M., & Radius, U. (2016). Synthesis and Thermal Properties of Novel NHC-Stabilized Cobalt Carbonyl Nitrosyl Complexes. Organometallics, 35, 2806-2821. https://doi.org/10.1021/acs.organomet.6b00374
Hopkinson, M., Richter, C., Schedler, M., & Glorius, F. (2014). An overview of N-heterocycli carbenes. Nature, 510, 485-496. https://doi.org/10.1038/nature13384
Housecroft, C., & Sharpe, A. (2012). Inorganic Chemistry. Harlow: Pearson.
Hu, C., & Wang, J. (2016). Methods in ezymology (Vol. 580). Cambridge: Academic Press. https://doi.org/10.1016/bs.mie.2016.06.005
Hu, Y., Zhou, B., & Wang, C. (2018). Inert C-H bond transformations enabled by organometallic manganese catalysis. Accounts Chem Res, 51(3), 816-827. https://doi.org/10.1021/acs.accounts.8b00028
Iglesias, M., & Oro, L. (2018). A leap forward in iridium-NHC catalysis: new horizons and mechanistic insights. Chem. Soc. Rev, 47, 2772-2808. https://doi.org/10.1039/C7S00743D
Ilies, L., Chen, Q., Zeng, X., & Nakamura, E. (2011). Cobalt-catalyzed chemoselective insertion of alkene into the ortho C-H bond of benzamide. J. Am. Chem. Soc, 133(14), 5221-5223. https://doi.org/10.1021/ja200645w
Kashyap, A., & Silakari, O. (2018). Chapter 9 - Triazoles: Multidimensional 5-Membered Nucleus for Designing Multitargeting Agents. En O. Silakari, Key Heterocycle Cores for Designing Multitargeting Molecules (págs. 323-342). Punjab: Elsevier. https://doi.org/10.1016/C2016-0-01252-4
Khiar, C., Tassadit, M., Bennini, L., Halouane, M, Benito, M., . . . Rabia, C. (2017). Cobalt supported on alumina as green catalyst for Biginelli reaction in mild conditions: effect of catalyst preparation method. Green Processing and Synthesis, 6(6), 533-541. https://doi.org/10.1515/gps-2016-0149
Killion, J., Darrow, W., Brennan, M., Leahy, C., & Fout, A. (2022). Cobalt-Catalyzed Kumada Coupling Forming Sterically Encumbered C–C Bonds. Organometallics, 41(14), 1769-1776. https://doi.org/10.1021/acs.organomet.1c00513
Knappke, C., Grupe, S., Gärtner, D., Corpet, M., Gosmini, C., & Von Wangelin, A. (2014). Reductive Cross-Coupling Reactions between Two Electrophiles. Chem. Eur. J, 20, 6828–6842. https://doi.org/10.1002/chem.201402302
Koy, M., Bellotti, P., & Das, M. &. (2021). N-Heterocyclic carbenes as tunable ligands for catalytic metal surfaces. Natura catalysis, 4, 352-363. https://doi.org/10.1038/s41929-021-00607-z
Lee, P., & Yoshikai, N. (2015). Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes. Org. Lett, 17(1), 22-25. https://doi.org/10.1021/ol503119z
Lewis, R., Koy, M., Macino, M., Das, M., Carter, J., Morgan, D., . . . Hutchings, G. (2022). N-Heterocyclic Carbene Modified Palladium Catalysts for the Direct Synthesis of Hydrogen Peroxide. Am. Chem. Soc, 144(34), 15431-15436. https://doi.org/10.1021/jacs.2c04828
Li, Y., Yu, S., Shen, W., & Gao, J. (2015). Iron-, Cobalt-, and Nickel-Catalyzed Asymmetric Transfer Hydrogenation and Asymmetric Hydrogenation of Ketones. Acc. Chem. Res, 48, 2587-2598. https://doi.org/10.1021/acs.accounts.5b00043
Liu, F., Zhong, J., Zhou, Y., Gao, Z. W., Wang, X., Ma, S., . . . Bian, Q. (2018). Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs. Chemistry, 9(24), 2059-2064. https://doi.org/10.1002/chem.201705463
Liu, Y., Friesen, J., McAlpine, J., Lankin, D., & Chen, S. &. (2018). Natural Deep Eutectic Solvents: Properties, Applications, and Perspectives. J. Nat. Prod, 81(3), 679-690. https://doi.org/10.1021/acs.jnatprod.7b00945
Ljardar, S., Singh, V., & Gardas, R. (2022). Revisiting the Physicochemical Properties and Applications of Deep Eutectic Solvents. Molecules, 27(4), 1368. https://doi.org/10.3390/molecules27041368
Lubitz, K., & Radius, U. (2019). The Coupling of N-Heterocyclic Carbenes to Terminal Alkynes at Half Sandwich Cobalt NHC Complexes. Organometallics, 38, 2558–2572. https://doi.org/10.1021/acs.organomet.9b00241
Lukasevics, L., Cizikovs, A., & Grigorieva, L. (2021). C-H Bond functionalization by high-valent Cobalt catalysis: current progress challenges and future perspectives. Chem. Commun, 57, 10827-10841. https://doi.org/10.1039/D1CC04382J
Luna, R. (2016). Estudio de complejos metal-carbeno mesoiónicos como catalizadores en condiciones medioambientalmente sostenibles. Alicante: Repositorio Universitat d' Alacant. http://hdl.handle.net/10045/56154
Luo, Y., Ma, H., Zhang, S., Zheng, D., Che, P., Liu, X., . . . Xu, J. (2020). Binding energy as driving force for controllable reconstruction of hydrogen bonds with molecular scissors. J. Am. Chem. Soc, 142, 6085–6092. https://doi.org/10.1021/jacs.9b12117
Marcus, Y. (2019). Deep eutectic solvents. Jerusalem: Springer. https://doi.org/10.1007/978-3-030-00608-2
Marset, X., & Guillena, G. (2022). Deep eutectic solvents as á-la-carte medium for transition-metal-catalyzed organic processes. Molecules, 27(23), 1-30. https://doi.org/10.3390/molecules27238445
Martinez-Olid, F., Herranz, R., Alcañiz, E., & Flores, J. (2015). España Patente nº WO2015197890A1.
Mathew, P., Neels, A., & Albrecht, M. (2008). 1,2,3-Triazolylidenes as Versatile Abnormal Carbene Ligands for Late Transition Metals. J. Am. Chem. Soc, 13534-13535. https://doi.org/10.1021/JA805781S
Mei, R., Dhawa, U., Samanta, R., Ma, W., Wencel-Delord, J., & Ackermann, L. (2020). Cobalt-catalyzed oxidative C-H activation: strategies and concepts. ChemSusChem, 13(13), 3306-3356. https://doi.org/10.1002/cssc.202000024
Mei, R., Wang, H., Warratx, S., Macgregor, S., & Ackermann, L. (2016). Cobalt-catalyzed oxidase C-H/N-H alkyne annulation: mechanistic insights and access to anticancer agents. Chem.–Eur, 22(20), 6759-6763. https://doi.org/10.1002/chem.201601101
Mills, L., Gygi, D., Ludwig, J., Simmons, E., Wisniewski, S., Kim, J., & Chirika, P. (2022). Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands. ACS Catal, 12(3), 1905-1918. https://doi.org/10.1021/acscatal.1c05586
Mills, M., & Barnes, C. B. (2018). Influences of Bifunctional PNP-Pincer Ligands on Low Valent Cobalt Complexes Relevant to CO2 Hydrogenation. Inorg. Chem, 57, 1590-1597. https://doi.org/10.1021/acs.inorgchem.7b02931
Mitsubayashi, K., Niwa, O., & Ueno, Y. (2019). Chemical, Gas, and Biosensors for Internet of Things and Related. Tokyo: Elsevier. https://doi.org/10.1016/C2017-0-03327-X
Moselage, M., Li, J., & Ackermann, L. (2016). Cobalt-catalyzed CeH activatio. ACS Catal, 6(2), 498-525. https://doi.org/10.1021/acscatal.5b02344
Mukherjee, A., & Milstein, D. (2018). Homogeneous Catalysis by Cobalt and Manganese Pincer Complexe. ACS catal, 8, 11435-11469. https://doi.org/10.1002/ejoc.201700376
Nasr-Esfahani, M., Montazerozohori, M., & Aghel-Mirrezaee, M. &. (2014). EFFICIENT AND GREEN CATALYTIC SYNTHESIS OF DIHYDROPYRIMIDINONE (THIONE) DERIVATIVES. J. Chil. Chem. Soc, 59(1), 2311-2314. https://doi.org/10.4067/S0717-97072014000100015
Nelson, D., & Nolan, S. (2014). N-Heterocyclic carbenes. En S. Nolan, N-Heterocyclic carbenes: effective tools for organometallic synthesis (págs. 1-24). St Andrews: Wiley-vch. https://doi.org/10.1002/9783527671229
Nielse, A., & Houlihan, W. (2011). The Aldol Condensation. Organic Reactions, 1-438. https://doi.org/10.1002/0471264180.or016.01
Nwe, K., & Brechbiel, M. (2009). Growing Applications of “Click Chemistry” for Bioconjugation in Contemporary Biomedical Research. Cancer Biother Radiopharm, 24(3), 289-302. https://doi.org/10.1089/cbr.2008.0626
Ogba, O., Warner, N., O'Leary, D., & Grubbs, R. (2018). Recent advances in ruthenium-based olefin metathesis. Chem. Soc. Rev, 47, 4510-4544. https://doi.org/10.1039/C8CS00027A
Peris, E. (2018). Smart N-Heterocyclic Carbene Ligands in Catalysis. Chem. Rev, 118, 9988-10031. https://doi.org/10.1021/acs.chemrev.6b00695
Picazo-Rodriguez, N., Toro, N., Garza Román, M., Tamayo, D., Galleguillos, F., Jamett, I., . . . Moreno, J. (2023). Cobalt Metal: Overview of Deposits, Reserves, Processing, and Recycling. Preprints, 06(01), 1-23. https://doi.org/10.20944/preprints202306.1368.v1
Ponce, S., Murillo, H., Alexis, F., Alvarez-Barreto, J., & Mora, J. (2023). Green Synthesis of Nanoparticles Mediated by Deep Eutectic Solvents and Their Applications in Water Treatment. Sustainabilit, 15(12), 1-18. https://doi.org/10.3390/su15129703
Prabhune, A., & Dey, R. (2023). Green and sustainable solvents of the future: Deep eutectic solvents. Journal of Molecular Liquids, 379(121676), 1-11. https://doi.org/10.1016/j.molliq.2023.121676
Puripat, M., Ramozzi, R., Hatanaka, M., Parasuk, W., Parasuk, V., & Morokuma, K. (2015). The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction. J. Org. Chem, 80(14), 6959-6967. https://doi.org/10.1021/acs.joc.5b00407
Quevedo, D. (2018). Síntesis de Monastrol y análogos, compuestos con potenciales. Tenerife: Universidad de La Laguna.
Rodionov, V. O., Fokin, V. V., & Finn, M. G. (2005). Mechanism of the Ligand-Free CuI-Catalyzed Azide-Alkyne Cycloaddition Reaction. Am. Ethnol, 117, 2250−2255. https://doi.org/10.1002/anie.200461496
Rokichki, G., & Parzuchowski, P. (2012). ROP of Cyclic Carbonates and ROP of Macrocycles. Polymer Science: A Comprehensive Reference, 4, 247-308. https://doi.org/10.1016/B978-0-12-803581-8.01381-3
Rubab, L., Anum, A., S, A.-H., A, I., S, A., Ullah, S., . . . Zaki, M. (2022). Green chesmitry in organic synthesis: recent upgrade on green catalytic approaches in synthesis 1,2,4-triadiazoles. Catalysts, 12(11), 1-24. https://doi.org/10.3390/catal12111329
Sakander, N., Ahmed, A., & Rasool, B. &. (2023). An Overview of N-heterocyclic carbene: Properties and Applications. IntechOpen, 1-19. https://doi.org/10.5772/intechopen.1001331
Sanchez-Sancho, F., Escolano, M., Gaviña, D, Csáky, A., Sánchez-Roselló, M., . . . Del Pozo, C. (2022). Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions. Pharmaceuticals, 15(8), 948. https://doi.org/10.3390/ph15080948
Sethiya, A., Sahiba, N., & Agarwaluna, S. (2021). Role of Click Chemistry in Organic Synthesis. Book Current Topics in Chirality - From Chemistry to Biology. Udaipur: IntechOpen. https://doi.org/10.5772/intechopen.96146
Simler, T., Choua, S., Danopoulos, A. A., & Braunstein, P. (2018). Reactivity of A Dearomatised Pincer CoIIBr Complex with PNCNHC Donors: Alkylation and Si-H Bond Activation via Metal-Ligand Cooperation. Dalton Trans, 47, 7888-7895. https://doi.org/10.1039/C8DT01279B
Smitt, E., Abbot, A., & Rydes, K. (2014). Deep Eutectic Solvents (DESs) and Their Applications. Chem. Rev, 114(21), 11060-11082. https://doi.org/10.1021/cr300162p
Stroek, W., Keilwerth, M., Pividori, D., Meyer, K., & Albrecht, M. (2021). An Iron–Mesoionic Carbene Complex for Catalytic Intramolecular C–H Amination Utilizing Organic Azides. J. Am. Chem. Soc, 143(48), 20157-20165. https://doi.org/10.1021/jacs.1c07378
Sweet, F., & Fissekis, J. (1973). Synthesis of 3,4-dihydro-2(1H)-pyrimidinones and the mechanism of the Biginelli reaction. J Am Chem Soc, 8741-8749. https://doi.org/10.1021/ja00807a040
Tasis, D., Tagmatarchis, N., & Bianco, A. &. (2006). Chemistry of carbon nanotubes. Chem. Rev, 106(3), 1105-1136. https://doi.org/10.1021/cr050569o
Tressaud, A. (2019). Fluorine: A Paradoxical Element. Bordeaux: Elsevier. https://doi.org/10.1016/B978-0-12-812990-6.00002-7
Urriolabeitia, E., & Ruiz, S. (2019). Ru (ii)-Catalysed synthesis of (1 H)- isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes. Org. Biomol. Chem., 17(9), 2542-2547. https://doi.org/10.1039/C8OB03201G
Védrine, J. (2018). Metal Oxides in Heterogeneous Catalysis. Paris: Elsevier. https://doi.org/10.1016/C2016-0-01790-4
Vivancos, A., Segarra, C., & Albrecht, M. (2018). Mesoionic and Related Less Heteroatom-Stabilized N-Heterocyclic Carbene Complexes: Synthesis, Catalysis, and Other Applications. Chem. Rev, 118(19), 9493-9586. https://doi.org/10.1021/acs.chemrev.8b00148
Wen, H., Liu, G., & Huang, Z. (2019). Recent advances in tridentate iron and cobalt complexes for alkene and alkyne hydrofunctionalizations. Coord. Chem. Rev, 386, 138-153. https://doi.org/10.1016/j.ccr.2019.01.024
Wen, J., Wang, D., Qian, J., Zhu, C., Zhao, Y., & Shi, Z. (2019). Rhodium-catalyzed PIII-directed ortho-C- H borylation of arylphosphines. Angew. Chem. Int. Ed., 58(7), 2078-2082. https://doi.org/10.1002/anie.201813452
Wu, C., Teo, W., & Ge, S. (2018). Cobalt-Catalyzed (E)-Selective anti Markovnikov hydrosilylation of terminal alkynes. ACS Catal, 8, 5896-5900. https://doi.org/10.1021/acscatal.8b01410
Yamada, K. (2013). Cobalt: Its role in health and diseases. Met Ions Life Sci, 13, 295-320. https://doi.org/10.1007/978-94-007-7500-8_9
Zhao, Q., Meng, C., Nolan, S., & Szostak, M. (2020). N-Heterocyclic Carbene Complexes in C–H Activation Reactions. Chem. Rev, 120, 1981-2048. https://doi.org/10.1021/acs.chemrev.9b00634
Zhu, Y., Dong, W., & Wenjun, T. (2022). Palladium-catalyzed cross-couplings in the synthesis of agrochemicals. Advanced Agrochem, 1(2), 125-138. https://doi.org/10.1016/j.aac.2022.11.004
dc.rights.*.fl_str_mv Atribución-NoComercial-CompartirIgual 2.5 Colombia
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by-nc-sa/2.5/co/
dc.rights.local.spa.fl_str_mv Abierto (Texto Completo)
dc.rights.accessrights.none.fl_str_mv info:eu-repo/semantics/openAccess
dc.rights.coar.spa.fl_str_mv http://purl.org/coar/access_right/c_abf2
rights_invalid_str_mv Atribución-NoComercial-CompartirIgual 2.5 Colombia
http://creativecommons.org/licenses/by-nc-sa/2.5/co/
Abierto (Texto Completo)
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.coverage.campus.spa.fl_str_mv CRAI-USTA Bucaramanga
dc.publisher.spa.fl_str_mv Universidad Santo Tomás
dc.publisher.program.spa.fl_str_mv Pregrado Química Ambiental
dc.publisher.faculty.spa.fl_str_mv Facultad de Química Ambiental
institution Universidad Santo Tomás
bitstream.url.fl_str_mv https://repository.usta.edu.co/bitstream/11634/53255/6/2023PradaLizeth.pdf.jpg
https://repository.usta.edu.co/bitstream/11634/53255/7/2023PradaLizeth1.pdf.jpg
https://repository.usta.edu.co/bitstream/11634/53255/8/2023PradaLizeth2.pdf.jpg
https://repository.usta.edu.co/bitstream/11634/53255/1/2023PradaLizeth.pdf
https://repository.usta.edu.co/bitstream/11634/53255/2/2023PradaLizeth1.pdf
https://repository.usta.edu.co/bitstream/11634/53255/3/2023PradaLizeth2.pdf
https://repository.usta.edu.co/bitstream/11634/53255/4/license_rdf
https://repository.usta.edu.co/bitstream/11634/53255/5/license.txt
bitstream.checksum.fl_str_mv 110ad9e0f65ab99bba22901dafa3fcfd
8992439f16d561764fdbdf08e6005dd1
2306326f821f7e21afc72a8f59506436
f53faba73c28851168b5f8ab6a477f91
69f17556e9f314294326d136d43a3dff
2a9be74ac70cebae6420c5b4ca574159
1487462a1490a8fc01f5999ce7b3b9cc
aedeaf396fcd827b537c73d23464fc27
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
MD5
MD5
MD5
MD5
MD5
repository.name.fl_str_mv Repositorio Universidad Santo Tomás
repository.mail.fl_str_mv noreply@usta.edu.co
_version_ 1860881968123609088
spelling Osorio Martínez, Carlos AlbertoAlvarado Rueda, Lizeth JohannaPrada Rojas, Lizeth Daniela2023-12-18T19:07:04Z2023-12-18T19:07:04Z2023-12-18Prada Rojas, L.D. (2023). Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sostenibles. [Trabajo de pregrado]. Universidad Santo Tomás, Bucaramanga, Colombia.http://hdl.handle.net/11634/53255reponame:Repositorio Institucional Universidad Santo Tomásinstname:Universidad Santo Tomásrepourl:https://repository.usta.edu.coLa optimización de reacciones químicas mediante el uso de catalizadores permite reducir los tiempos de reacción e incrementar el rendimiento de estas. Los catalizadores homogéneos de tipo metal-carbeno NHC mesoiónicos, suelen presentar una alta selectividad, una actividad mejorada y mejor estabilidad en comparación con sistemas análogos más clásicos en los que se utilizan ligandos de organofosfina. El principal impacto negativo en la síntesis de catalizadores es la utilización de solventes orgánicos, por lo que se ha propuesto el uso de solventes eutécticos profundos (DES), los cuales suelen estar constituidos por dos o tres compuestos; una sal de amonio cuaternaria complejada con un compuesto donor de hidrogeno o una sal metálica. En este trabajo, se planteó la síntesis de un catalizador de tipo metal-carbeno NHC mesoiónico mediante una serie de reacciones “click chemistry”, metilación y reacciones de acomplejación con un metal de transición por vía tradicional y por vía DES. Los compuestos obtenidos se caracterización mediante infrarrojo, resonancia magnética y puntos de fusión. Y se evaluó la actividad catalítica del metal-carbenoNHC obtenido en reacciones de Biginelli. Estos procesos se compararon en términos de rendimientos de reacción. La complejación del catalizador se vio favorecida por el uso de DES, pese a que en la “Click chemistry” y la metilación el rendimiento fue menor a que por la vía tradicional. Para poder evaluar su actividad catalítica es necesario continuar probando con diferentes reacciones.The optimization of chemical reactions using catalysts allows to reduce reaction times and increase reaction yields. Homogeneous mesoionic NHC metal-carbene catalysts usually show high selectivity, improved activity and better stability compared to more classical analogous systems using organophosphine ligands. The main negative impact in the synthesis of catalysts is the use of organic solvents, so the use of deep eutectic solvents (DESs) has been proposed, which usually consist of two or three compounds; a quaternary ammonium salt complexed with a hydrogen donor compound or a metal salt. In this work, the synthesis of a mesoionic NHC metal-carbene catalyst by a series of "click chemistry" reactions, methylation, and complexation reactions with a transition metal by traditional and DES routes were proposed. The obtained compounds were characterized by infrared, magnetic resonance and melting points. And the catalytic activity of the metal-carbene-NHC obtained in Biginelli reactions was evaluated. These processes were compared in terms of reaction yields. The complexation of the catalyst was favored using DES, although in click chemistry and methylation the yield was lower than by the traditional route. To evaluate its catalytic activity, it is necessary to continue testing with different reactions.Químico Ambientalhttp://www.ustabuca.edu.co/ustabmanga/presentacionPregradoapplication/pdfspaUniversidad Santo TomásPregrado Química AmbientalFacultad de Química AmbientalAtribución-NoComercial-CompartirIgual 2.5 Colombiahttp://creativecommons.org/licenses/by-nc-sa/2.5/co/Abierto (Texto Completo)info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Síntesis de catalizadores metal-carbenos N-heterocíclicos (NHC) y evaluación de su actividad catalítica en condiciones ambientalmente sosteniblesCatalystMethylationDESCobalt-NHCCarbenesolventes orgánicoscatalizadoresreacciones químicasreacciones orgánicasCatalizadorMetilaciónDESCobalto-NHCCarbenoTrabajo de gradoinfo:eu-repo/semantics/acceptedVersionFormación de Recurso Humano para la Ctel: Trabajo de grado de Pregradohttp://purl.org/coar/resource_type/c_7a1finfo:eu-repo/semantics/bachelorThesisCRAI-USTA BucaramangaAguilera, E. (2021). Derivados de monastrol a partir de β-cetoésteres lipofilicos por la reacción de Biginelli. Investigación Joven, 8(2), 26-32.Akter, M., Rupa, K., & Anbasaran, P. (2022). 1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds. Chem. Rev, 122(15), 13108-13205. https://doi.org/10.1021/acs.chemrev.1c00991Alonso, D., Baeza, A., Chinchilla, R., Gómez, C., Guillena, G., Marset, X., . . . Saavedra, B. (2018). Mezclas eutécticas como alternativa sostenible a los disolventes. An. Quim, 79-87.Andruch, V., Varvfalvyová, A. H., Jatkowska, N., & Płotka-Wasylka, J. (2022). Application of deep eutectic solvents in bioanalysis. Trends in Analytical. Trends in Analytical Chemistry, 154(116660), 1-19. https://doi.org/10.1016/j.trac.2022.116660Aravena, C., Lee, D., Park, J., & Yoo, Y. (2022). Characteristics of Deep eutectic solvents for CO2 capture with Hydro effects for improvement of mass transfer. Journal of industrial and engineering chemistry, 111, 337-345. https://doi.org/10.1016/j.jiec.2022.04.015Arnold, J., Brothers, P., Mountford, P., Piers, W., Thomas, C., & Tilley, T. (2014). The influence of Michael Lappert on the chemistry landscape. Dalton Trans, 43(44), 16533-16556. https://doi.org/10.1039/C4DT90167CBellotti, P., Koy, M., & Hopkinson, M. &. (2021). Recent advances in the chemistry and applications of N-heterocyclic carbenes. Nat. Rev. Chem, 5, 711-725. https://doi.org/10.1038/s41570-021-00321-1Bera, S., & Szotak, M. (2022). Cobalt-N-Heterocyclic carbene complex in catalysis. ACS Catal, 12(5), 3111-3137. https://doi.org/10.1021/acscatal.1c05869Bharti, R., Verme, M., Thakys, A., & Sharma, R. (2022). N-Heterocyclic Carbenes (NHCs): An Introduction. Varanasi: IntechOpen. https://doi.org/10.5772/intechopen.102760Bhujabal, Y., Vadagaonkar, K., & Kapdi, A. (2019). Pd/PTABS: catalyst for efficient C-H (hetero) arylation of 1, 3, 4-oxadiazoles using bromo (hetero) arenes. Asian Journal of Organic Chemistry, 8(2), 289-295. https://doi.org/10.1002/ajoc.201800713Binandeh, M., Nasseri, M., & Allahresani, A. (2022). High-Power and High-Performance Catalyst for Suzuki Coupling Reaction. Catalysts, 12(9), 1-13. https://doi.org/10.3390/catal12090976Chen, Y., & Mu, T. (2019). Application of deep eutectic solvents in biomass pretreatment and conversion. Green. Energy Environ, 4, 95-115. https://doi.org/10.1016/j.gee.2019.01.012Chorkendorff, I., & Niemantsverdriet, J. (2017). Concepts of Modern Catalysis and Kinetics. Wiley VCH.Contreras, R. (2021). Catálisis homogénea con metales de transición: transformando el mundo de la química. Mérida: CDCHTA.Corrigan, N., Zhernakov, L., Hashim, M., Xu, J., & Boyer, C. (2019). Flow mediated metal free PET-RAFT polymerisation for upscaled and consistent polymer production. Reaction Chemistry & Engineering, 4(7), 1216-1228. https://doi.org/10.1039/C9RE00014CCrabtree, R. (2013). Abnormal, mesoionic and remote N-heterocyclic carbene complexes. Coordination Chemistry Reviews, 257, 755-766. https://doi.org/10.1016/j.ccr.2012.09.006Dalko, P. (2013). Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications. Wiley‐VCH. https://doi.org/10.1002/9783527658862Danopoulos, A., Massard, G., Frison, G., & Braunstein, P. (2018). Iron and Cobalt Metallotropism in Remote-Substituted NHC Ligands: Metalation to Abnormal NHC Complexes or NHC Ring Opening. Angew. Chem. Int. Ed, 57, 14550-14554. https://doi.org/10.1002/anie.201808008Danopoulos, A., Simler, T., & Braunstein, P. (2019). N-Hetercyclic carbene complexes of copper, nickel and cobalt. Chem. Rev, 119, 3730-3961. https://doi.org/10.1021/acs.chemrev.8b00505De Fatima, A., Cafiero, T., Silva, B., & Da Silva, L. (2021). Green Synthetic Approaches for Biologically Relevant Heterocycles. Santiniketan: Elsevier. https://doi.org/10.1016/C2018-0-05415-8De Frémont, P., Marion, N., Nolan, & S. (2009). Carbenes: Synthesis, properties, and organometallic chemistry. Coordin. Chem. Rev, 253, 862-892. https://doi.org/10.1016/j.ccr.2008.05.018Devaraj, N., & Finn, M. (2021). Introduction: Click Chemistry. Chem. Rev, 121(12), 6697-6698. https://doi.org/10.1021/acs.chemrev.1c00469Díez‐González, S. (2016). N-heterocyclic carbenes : from laboratory curiosities to efficient synthetic tools. London: The Royal Society of Chemistry. https://doi.org/10.1039/9781782626817Dongkun, Y., Zhimin, X., & Tiancheng, M. (2022). Deep eutectic solvents as a green toolbox for synthesis. Cell Reports Physical Science, 3(100809), 1-23. https://doi.org/10.1016/j.xcrp.2022.100809Du, J., Wang, L., & Xie, M. &. (2015). A Two-Coordinate Cobalt(II) Imido Complex with NHC Ligation: Synthesis, Structure, and Reactivity. Angew. Chem. Int. Ed, 54, 12640-12644. https://doi.org/10.1002/anie.201505937El Achkar, T., Greige Gerges, H., & Fourmentin, S. (2022). Basics and properties of deep eutectic solvents: a review. Basics and properties of deep eutectic solvents: a review, 19(29), 3397-3408. https://doi.org/10.1007/s10311-021-01225-8EPA. (9 de Mayo de 2023). EPA. EPA.gov: https://www.epa.gov/greenchemistry/basics-green-chemistry#:~:text=Green%20chemistry%20is%20the%20design,%2C%20use%2C%20and%20ultimate%20disposal.Fürstner, A. (2016). Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion. ACS Cent. Sci, 2(11), 778-789. https://doi.org/10.1021/acscentsci.6b00272Girard, S., Knauber, T., & Li, C. (2014). The cross-dehydrogenative coupling of C (sp3)- H bonds: a versatile strategy for C-C bond formations. Angew. Chem. Int. Ed., 53(1), 74-100. https://doi.org/10.1002/anie.201304268Gronert, S., Keeffe, J., & More O'Ferrall, R. (2011). Stabilities of Carbenes: Independent Measures for Singlets and Triplets. J. Am. Chem. Soc, 133(10), 3381-3389. https://doi.org/10.1021/ja1071493Guo, L., Srimontree, W., Zhu, C., Maity, B., Xiangqian, L., Cavallo, L., & Rueping, M. (2019). Nickel-catalyzed Suzuki–Miyaura cross-couplings of aldehydes. Nature Communications, 10(1957), 1-6. https://doi.org/10.1038/s41467-019-09766-xHameury, S., P, D. F., & Braunstein, P. (2017). Metal complexes with oxygen-functionalized NHC ligands: synthesis and applications. Chem. Soc. Rev, 46, 632-733. https://doi.org/10.1039/C6CS00499GHammond, O., Bowron, D., & Edler, K. (2017). The Effect of Water upon Deep Eutectic Solvent Nanostructure: An Unusual Transition from Ionic Mixture to Aqueous Solution. Angew. Chem. Int, 56, 9782-9785. https://doi.org/10.1002/anie.201702486Hansen, B. S., Klein, J., Horton, A., Adhikari, L., Zelovich, T., Doherty, B., & al, e. (2021). Deep eutectic solvents: a review of fundamentals and application. Chem. Rev, 1232-1285. https://doi.org/10.1021/acs.chemrev.0c00385Hasan, A., & Pandey, L. (2014). Nanobiomaterials: Nanostructured Materials for Biomedical Applications. Guwahati: Elsevier. https://doi.org/10.1016/C2015-0-01648-3Hering, F., Berthel, J. H., Lubitz, K., Paul, U. S., Schneider, H., Harterich, M., & Radius, U. (2016). Synthesis and Thermal Properties of Novel NHC-Stabilized Cobalt Carbonyl Nitrosyl Complexes. Organometallics, 35, 2806-2821. https://doi.org/10.1021/acs.organomet.6b00374Hopkinson, M., Richter, C., Schedler, M., & Glorius, F. (2014). An overview of N-heterocycli carbenes. Nature, 510, 485-496. https://doi.org/10.1038/nature13384Housecroft, C., & Sharpe, A. (2012). Inorganic Chemistry. Harlow: Pearson.Hu, C., & Wang, J. (2016). Methods in ezymology (Vol. 580). Cambridge: Academic Press. https://doi.org/10.1016/bs.mie.2016.06.005Hu, Y., Zhou, B., & Wang, C. (2018). Inert C-H bond transformations enabled by organometallic manganese catalysis. Accounts Chem Res, 51(3), 816-827. https://doi.org/10.1021/acs.accounts.8b00028Iglesias, M., & Oro, L. (2018). A leap forward in iridium-NHC catalysis: new horizons and mechanistic insights. Chem. Soc. Rev, 47, 2772-2808. https://doi.org/10.1039/C7S00743DIlies, L., Chen, Q., Zeng, X., & Nakamura, E. (2011). Cobalt-catalyzed chemoselective insertion of alkene into the ortho C-H bond of benzamide. J. Am. Chem. Soc, 133(14), 5221-5223. https://doi.org/10.1021/ja200645wKashyap, A., & Silakari, O. (2018). Chapter 9 - Triazoles: Multidimensional 5-Membered Nucleus for Designing Multitargeting Agents. En O. Silakari, Key Heterocycle Cores for Designing Multitargeting Molecules (págs. 323-342). Punjab: Elsevier. https://doi.org/10.1016/C2016-0-01252-4Khiar, C., Tassadit, M., Bennini, L., Halouane, M, Benito, M., . . . Rabia, C. (2017). Cobalt supported on alumina as green catalyst for Biginelli reaction in mild conditions: effect of catalyst preparation method. Green Processing and Synthesis, 6(6), 533-541. https://doi.org/10.1515/gps-2016-0149Killion, J., Darrow, W., Brennan, M., Leahy, C., & Fout, A. (2022). Cobalt-Catalyzed Kumada Coupling Forming Sterically Encumbered C–C Bonds. Organometallics, 41(14), 1769-1776. https://doi.org/10.1021/acs.organomet.1c00513Knappke, C., Grupe, S., Gärtner, D., Corpet, M., Gosmini, C., & Von Wangelin, A. (2014). Reductive Cross-Coupling Reactions between Two Electrophiles. Chem. Eur. J, 20, 6828–6842. https://doi.org/10.1002/chem.201402302Koy, M., Bellotti, P., & Das, M. &. (2021). N-Heterocyclic carbenes as tunable ligands for catalytic metal surfaces. Natura catalysis, 4, 352-363. https://doi.org/10.1038/s41929-021-00607-zLee, P., & Yoshikai, N. (2015). Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes. Org. Lett, 17(1), 22-25. https://doi.org/10.1021/ol503119zLewis, R., Koy, M., Macino, M., Das, M., Carter, J., Morgan, D., . . . Hutchings, G. (2022). N-Heterocyclic Carbene Modified Palladium Catalysts for the Direct Synthesis of Hydrogen Peroxide. Am. Chem. Soc, 144(34), 15431-15436. https://doi.org/10.1021/jacs.2c04828Li, Y., Yu, S., Shen, W., & Gao, J. (2015). Iron-, Cobalt-, and Nickel-Catalyzed Asymmetric Transfer Hydrogenation and Asymmetric Hydrogenation of Ketones. Acc. Chem. Res, 48, 2587-2598. https://doi.org/10.1021/acs.accounts.5b00043Liu, F., Zhong, J., Zhou, Y., Gao, Z. W., Wang, X., Ma, S., . . . Bian, Q. (2018). Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs. Chemistry, 9(24), 2059-2064. https://doi.org/10.1002/chem.201705463Liu, Y., Friesen, J., McAlpine, J., Lankin, D., & Chen, S. &. (2018). Natural Deep Eutectic Solvents: Properties, Applications, and Perspectives. J. Nat. Prod, 81(3), 679-690. https://doi.org/10.1021/acs.jnatprod.7b00945Ljardar, S., Singh, V., & Gardas, R. (2022). Revisiting the Physicochemical Properties and Applications of Deep Eutectic Solvents. Molecules, 27(4), 1368. https://doi.org/10.3390/molecules27041368Lubitz, K., & Radius, U. (2019). The Coupling of N-Heterocyclic Carbenes to Terminal Alkynes at Half Sandwich Cobalt NHC Complexes. Organometallics, 38, 2558–2572. https://doi.org/10.1021/acs.organomet.9b00241Lukasevics, L., Cizikovs, A., & Grigorieva, L. (2021). C-H Bond functionalization by high-valent Cobalt catalysis: current progress challenges and future perspectives. Chem. Commun, 57, 10827-10841. https://doi.org/10.1039/D1CC04382JLuna, R. (2016). Estudio de complejos metal-carbeno mesoiónicos como catalizadores en condiciones medioambientalmente sostenibles. Alicante: Repositorio Universitat d' Alacant. http://hdl.handle.net/10045/56154Luo, Y., Ma, H., Zhang, S., Zheng, D., Che, P., Liu, X., . . . Xu, J. (2020). Binding energy as driving force for controllable reconstruction of hydrogen bonds with molecular scissors. J. Am. Chem. Soc, 142, 6085–6092. https://doi.org/10.1021/jacs.9b12117Marcus, Y. (2019). Deep eutectic solvents. Jerusalem: Springer. https://doi.org/10.1007/978-3-030-00608-2Marset, X., & Guillena, G. (2022). Deep eutectic solvents as á-la-carte medium for transition-metal-catalyzed organic processes. Molecules, 27(23), 1-30. https://doi.org/10.3390/molecules27238445Martinez-Olid, F., Herranz, R., Alcañiz, E., & Flores, J. (2015). España Patente nº WO2015197890A1.Mathew, P., Neels, A., & Albrecht, M. (2008). 1,2,3-Triazolylidenes as Versatile Abnormal Carbene Ligands for Late Transition Metals. J. Am. Chem. Soc, 13534-13535. https://doi.org/10.1021/JA805781SMei, R., Dhawa, U., Samanta, R., Ma, W., Wencel-Delord, J., & Ackermann, L. (2020). Cobalt-catalyzed oxidative C-H activation: strategies and concepts. ChemSusChem, 13(13), 3306-3356. https://doi.org/10.1002/cssc.202000024Mei, R., Wang, H., Warratx, S., Macgregor, S., & Ackermann, L. (2016). Cobalt-catalyzed oxidase C-H/N-H alkyne annulation: mechanistic insights and access to anticancer agents. Chem.–Eur, 22(20), 6759-6763. https://doi.org/10.1002/chem.201601101Mills, L., Gygi, D., Ludwig, J., Simmons, E., Wisniewski, S., Kim, J., & Chirika, P. (2022). Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands. ACS Catal, 12(3), 1905-1918. https://doi.org/10.1021/acscatal.1c05586Mills, M., & Barnes, C. B. (2018). Influences of Bifunctional PNP-Pincer Ligands on Low Valent Cobalt Complexes Relevant to CO2 Hydrogenation. Inorg. Chem, 57, 1590-1597. https://doi.org/10.1021/acs.inorgchem.7b02931Mitsubayashi, K., Niwa, O., & Ueno, Y. (2019). Chemical, Gas, and Biosensors for Internet of Things and Related. Tokyo: Elsevier. https://doi.org/10.1016/C2017-0-03327-XMoselage, M., Li, J., & Ackermann, L. (2016). Cobalt-catalyzed CeH activatio. ACS Catal, 6(2), 498-525. https://doi.org/10.1021/acscatal.5b02344Mukherjee, A., & Milstein, D. (2018). Homogeneous Catalysis by Cobalt and Manganese Pincer Complexe. ACS catal, 8, 11435-11469. https://doi.org/10.1002/ejoc.201700376Nasr-Esfahani, M., Montazerozohori, M., & Aghel-Mirrezaee, M. &. (2014). EFFICIENT AND GREEN CATALYTIC SYNTHESIS OF DIHYDROPYRIMIDINONE (THIONE) DERIVATIVES. J. Chil. Chem. Soc, 59(1), 2311-2314. https://doi.org/10.4067/S0717-97072014000100015Nelson, D., & Nolan, S. (2014). N-Heterocyclic carbenes. En S. Nolan, N-Heterocyclic carbenes: effective tools for organometallic synthesis (págs. 1-24). St Andrews: Wiley-vch. https://doi.org/10.1002/9783527671229Nielse, A., & Houlihan, W. (2011). The Aldol Condensation. Organic Reactions, 1-438. https://doi.org/10.1002/0471264180.or016.01Nwe, K., & Brechbiel, M. (2009). Growing Applications of “Click Chemistry” for Bioconjugation in Contemporary Biomedical Research. Cancer Biother Radiopharm, 24(3), 289-302. https://doi.org/10.1089/cbr.2008.0626Ogba, O., Warner, N., O'Leary, D., & Grubbs, R. (2018). Recent advances in ruthenium-based olefin metathesis. Chem. Soc. Rev, 47, 4510-4544. https://doi.org/10.1039/C8CS00027APeris, E. (2018). Smart N-Heterocyclic Carbene Ligands in Catalysis. Chem. Rev, 118, 9988-10031. https://doi.org/10.1021/acs.chemrev.6b00695Picazo-Rodriguez, N., Toro, N., Garza Román, M., Tamayo, D., Galleguillos, F., Jamett, I., . . . Moreno, J. (2023). Cobalt Metal: Overview of Deposits, Reserves, Processing, and Recycling. Preprints, 06(01), 1-23. https://doi.org/10.20944/preprints202306.1368.v1Ponce, S., Murillo, H., Alexis, F., Alvarez-Barreto, J., & Mora, J. (2023). Green Synthesis of Nanoparticles Mediated by Deep Eutectic Solvents and Their Applications in Water Treatment. Sustainabilit, 15(12), 1-18. https://doi.org/10.3390/su15129703Prabhune, A., & Dey, R. (2023). Green and sustainable solvents of the future: Deep eutectic solvents. Journal of Molecular Liquids, 379(121676), 1-11. https://doi.org/10.1016/j.molliq.2023.121676Puripat, M., Ramozzi, R., Hatanaka, M., Parasuk, W., Parasuk, V., & Morokuma, K. (2015). The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction. J. Org. Chem, 80(14), 6959-6967. https://doi.org/10.1021/acs.joc.5b00407Quevedo, D. (2018). Síntesis de Monastrol y análogos, compuestos con potenciales. Tenerife: Universidad de La Laguna.Rodionov, V. O., Fokin, V. V., & Finn, M. G. (2005). Mechanism of the Ligand-Free CuI-Catalyzed Azide-Alkyne Cycloaddition Reaction. Am. Ethnol, 117, 2250−2255. https://doi.org/10.1002/anie.200461496Rokichki, G., & Parzuchowski, P. (2012). ROP of Cyclic Carbonates and ROP of Macrocycles. Polymer Science: A Comprehensive Reference, 4, 247-308. https://doi.org/10.1016/B978-0-12-803581-8.01381-3Rubab, L., Anum, A., S, A.-H., A, I., S, A., Ullah, S., . . . Zaki, M. (2022). Green chesmitry in organic synthesis: recent upgrade on green catalytic approaches in synthesis 1,2,4-triadiazoles. Catalysts, 12(11), 1-24. https://doi.org/10.3390/catal12111329Sakander, N., Ahmed, A., & Rasool, B. &. (2023). An Overview of N-heterocyclic carbene: Properties and Applications. IntechOpen, 1-19. https://doi.org/10.5772/intechopen.1001331Sanchez-Sancho, F., Escolano, M., Gaviña, D, Csáky, A., Sánchez-Roselló, M., . . . Del Pozo, C. (2022). Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions. Pharmaceuticals, 15(8), 948. https://doi.org/10.3390/ph15080948Sethiya, A., Sahiba, N., & Agarwaluna, S. (2021). Role of Click Chemistry in Organic Synthesis. Book Current Topics in Chirality - From Chemistry to Biology. Udaipur: IntechOpen. https://doi.org/10.5772/intechopen.96146Simler, T., Choua, S., Danopoulos, A. A., & Braunstein, P. (2018). Reactivity of A Dearomatised Pincer CoIIBr Complex with PNCNHC Donors: Alkylation and Si-H Bond Activation via Metal-Ligand Cooperation. Dalton Trans, 47, 7888-7895. https://doi.org/10.1039/C8DT01279BSmitt, E., Abbot, A., & Rydes, K. (2014). Deep Eutectic Solvents (DESs) and Their Applications. Chem. Rev, 114(21), 11060-11082. https://doi.org/10.1021/cr300162pStroek, W., Keilwerth, M., Pividori, D., Meyer, K., & Albrecht, M. (2021). An Iron–Mesoionic Carbene Complex for Catalytic Intramolecular C–H Amination Utilizing Organic Azides. J. Am. Chem. Soc, 143(48), 20157-20165. https://doi.org/10.1021/jacs.1c07378Sweet, F., & Fissekis, J. (1973). Synthesis of 3,4-dihydro-2(1H)-pyrimidinones and the mechanism of the Biginelli reaction. J Am Chem Soc, 8741-8749. https://doi.org/10.1021/ja00807a040Tasis, D., Tagmatarchis, N., & Bianco, A. &. (2006). Chemistry of carbon nanotubes. Chem. Rev, 106(3), 1105-1136. https://doi.org/10.1021/cr050569oTressaud, A. (2019). Fluorine: A Paradoxical Element. Bordeaux: Elsevier. https://doi.org/10.1016/B978-0-12-812990-6.00002-7Urriolabeitia, E., & Ruiz, S. (2019). Ru (ii)-Catalysed synthesis of (1 H)- isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes. Org. Biomol. Chem., 17(9), 2542-2547. https://doi.org/10.1039/C8OB03201GVédrine, J. (2018). Metal Oxides in Heterogeneous Catalysis. Paris: Elsevier. https://doi.org/10.1016/C2016-0-01790-4Vivancos, A., Segarra, C., & Albrecht, M. (2018). Mesoionic and Related Less Heteroatom-Stabilized N-Heterocyclic Carbene Complexes: Synthesis, Catalysis, and Other Applications. Chem. Rev, 118(19), 9493-9586. https://doi.org/10.1021/acs.chemrev.8b00148Wen, H., Liu, G., & Huang, Z. (2019). Recent advances in tridentate iron and cobalt complexes for alkene and alkyne hydrofunctionalizations. Coord. Chem. Rev, 386, 138-153. https://doi.org/10.1016/j.ccr.2019.01.024Wen, J., Wang, D., Qian, J., Zhu, C., Zhao, Y., & Shi, Z. (2019). Rhodium-catalyzed PIII-directed ortho-C- H borylation of arylphosphines. Angew. Chem. Int. Ed., 58(7), 2078-2082. https://doi.org/10.1002/anie.201813452Wu, C., Teo, W., & Ge, S. (2018). Cobalt-Catalyzed (E)-Selective anti Markovnikov hydrosilylation of terminal alkynes. ACS Catal, 8, 5896-5900. https://doi.org/10.1021/acscatal.8b01410Yamada, K. (2013). Cobalt: Its role in health and diseases. Met Ions Life Sci, 13, 295-320. https://doi.org/10.1007/978-94-007-7500-8_9Zhao, Q., Meng, C., Nolan, S., & Szostak, M. (2020). N-Heterocyclic Carbene Complexes in C–H Activation Reactions. Chem. Rev, 120, 1981-2048. https://doi.org/10.1021/acs.chemrev.9b00634Zhu, Y., Dong, W., & Wenjun, T. (2022). Palladium-catalyzed cross-couplings in the synthesis of agrochemicals. Advanced Agrochem, 1(2), 125-138. https://doi.org/10.1016/j.aac.2022.11.004THUMBNAIL2023PradaLizeth.pdf.jpg2023PradaLizeth.pdf.jpgIM Thumbnailimage/jpeg5231https://repository.usta.edu.co/bitstream/11634/53255/6/2023PradaLizeth.pdf.jpg110ad9e0f65ab99bba22901dafa3fcfdMD56open access2023PradaLizeth1.pdf.jpg2023PradaLizeth1.pdf.jpgIM Thumbnailimage/jpeg8023https://repository.usta.edu.co/bitstream/11634/53255/7/2023PradaLizeth1.pdf.jpg8992439f16d561764fdbdf08e6005dd1MD57open access2023PradaLizeth2.pdf.jpg2023PradaLizeth2.pdf.jpgIM Thumbnailimage/jpeg8371https://repository.usta.edu.co/bitstream/11634/53255/8/2023PradaLizeth2.pdf.jpg2306326f821f7e21afc72a8f59506436MD58open accessORIGINAL2023PradaLizeth.pdf2023PradaLizeth.pdfTrabajo de gradoapplication/pdf4451397https://repository.usta.edu.co/bitstream/11634/53255/1/2023PradaLizeth.pdff53faba73c28851168b5f8ab6a477f91MD51open access2023PradaLizeth1.pdf2023PradaLizeth1.pdfAprobación Facultadapplication/pdf143825https://repository.usta.edu.co/bitstream/11634/53255/2/2023PradaLizeth1.pdf69f17556e9f314294326d136d43a3dffMD52metadata only access2023PradaLizeth2.pdf2023PradaLizeth2.pdfAcuerdo de Pubblicaciónapplication/pdf133960https://repository.usta.edu.co/bitstream/11634/53255/3/2023PradaLizeth2.pdf2a9be74ac70cebae6420c5b4ca574159MD53metadata only accessCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-81037https://repository.usta.edu.co/bitstream/11634/53255/4/license_rdf1487462a1490a8fc01f5999ce7b3b9ccMD54open accessLICENSElicense.txtlicense.txttext/plain; charset=utf-8807https://repository.usta.edu.co/bitstream/11634/53255/5/license.txtaedeaf396fcd827b537c73d23464fc27MD55open access11634/53255oai:repository.usta.edu.co:11634/532552023-12-19 03:05:23.759open accessRepositorio Universidad Santo Tomásnoreply@usta.edu.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

Publicaciones similares