Greco, R.; Tiburcio, E.; Palomar-De Lucas, B.; Ferrando-Soria, J.; Armentano, D.; Pardo, E.; Leyva Perez, A. (2022). Click amidations, esterifications and one¿pot reactions catalyzed by Cu salts and multimetal-organic frameworks (M-MOFs). Molecular Catalysis. 522:1-11. https://doi.org/10.1016/j.mcat.2022.112228
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/195597
Title:
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Click amidations, esterifications and one¿pot reactions catalyzed by Cu salts and multimetal-organic frameworks (M-MOFs)
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Author:
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Greco, Rossella
Tiburcio, Estefanía
Palomar-De Lucas, Brenda
Ferrando-Soria, Jesús
Armentano, Donatella
Pardo, Emilio
Leyva Perez, Antonio
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Issued date:
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Abstract:
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[EN] Amides and esters are prevalent chemicals in Nature, industry and academic laboratories. Thus, it is not surprising that a plethora of synthetic methods for these compounds has been developed along the years. However, ...[+]
[EN] Amides and esters are prevalent chemicals in Nature, industry and academic laboratories. Thus, it is not surprising that a plethora of synthetic methods for these compounds has been developed along the years. However, these methods are not 100% atom economical and generally require harsh reagents or reaction conditions. Here we show a "spring-loaded", 100% atom-efficient amidation and esterification protocol which consists in the ring opening of cyclopropenones with amines or alcohols. Some alkyl amines react spontaneously at room temperature in a variety of solvents and reaction conditions, including water at different pHs, while other alkyl amines, aromatic amines and alcohols react in the presence of catalytic amounts of simple Cu2+ salts or solids. A modular reactivity pattern (alkyl amines >> alkyl alcohols >> phenols >> aromatic amines) enables to design orthogonal and one-pot reactions on well-defined catalytic Multimetal-Organic Frameworks (M-MOFs, M= Cu, Ni, Pd), to easily functionalize the resulting cinnamides and cinnamic esters to more complex molecules. The strong resemblance of the amidation and esterification reaction conditions here reported with the copper-catalyzed azide-alkyne cycloaddition (CuAAC) allows to define this fast, clean and flexible protocol as a click reaction.
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Subjects:
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Click reaction
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Catalysis
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Metal-organic frameworks
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Cyclopropenones esters
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Amides
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Copper
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One-pot reactions
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Copyrigths:
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Reconocimiento - No comercial - Sin obra derivada (by-nc-nd)
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Source:
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Molecular Catalysis. (issn:
2468-8231
)
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DOI:
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10.1016/j.mcat.2022.112228
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Publisher:
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Elsevier
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Publisher version:
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https://doi.org/10.1016/j.mcat.2022.112228
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Project ID:
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info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104778GB-I00/ES/DESARROLLO DE POLIMEROS DE COORDINACION POROSOS FUNCIONALES CON APLICACIONES TECNOLOGICAS Y MEDIOAMBIENTALES/
...[+]
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104778GB-I00/ES/DESARROLLO DE POLIMEROS DE COORDINACION POROSOS FUNCIONALES CON APLICACIONES TECNOLOGICAS Y MEDIOAMBIENTALES/
info:eu-repo/grantAgreement/GVA//SEJI%2F2020%2F034/
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-115100GB-I00/ES/CLUSTERES CATALITICOS MULTIMETALICOS Y DE ALTA ENTROPIA PARA SINTESIS ORGANICA/
info:eu-repo/grantAgreement/MCIU//RTC-2017-6331-5//NUEVA SINTESIS DEL OLIGOMERO CLAVE EN TINTAS DIGITALES/
info:eu-repo/grantAgreement/EC/H2020/814804/EU
info:eu-repo/grantAgreement/MCIU//SEV-2016-0683/
info:eu-repo/grantAgreement/Fundació Bancària Caixa d'Estalvis i Pensions de Barcelona//ID100010434/
info:eu-repo/grantAgreement/Fundació Bancària Caixa d'Estalvis i Pensions de Barcelona//LCF%2FBQ%2FPR19%2F11700011/
info:eu-repo/grantAgreement/Fondazione Cariplo//2019-2090/
info:eu-repo/grantAgreement/MICINN//CEX2019-000919-M/
info:eu-repo/grantAgreement/DLS//CY22411-1/
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Thanks:
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This work was supported by the Ministero dell'Istruzione, dell'Universit`a e della Ricerca (Italy) and the MINECO (Spain) (Projects PID2019-104778GB-I00, RTC-2017-6331-5, Severo Ochoa program SEV-2016-0683 and Excellence ...[+]
This work was supported by the Ministero dell'Istruzione, dell'Universit`a e della Ricerca (Italy) and the MINECO (Spain) (Projects PID2019-104778GB-I00, RTC-2017-6331-5, Severo Ochoa program SEV-2016-0683 and Excellence Unit "Maria de Maeztu" CEX2019-000919-M) and MCIINN (Spain) (Project PID2020-115100GB-I00). D.A. acknowledgs the financial support of the Fondazione CARIPLO/"Economia Circolare: ricerca per un futuro sostenibile" 2019, Project code: 2019-2090, MOCA and Diamond Light Source for awarded beamtime and provision of synchrotron radiation facilities and thank Dr David Allan and Sarah Barnett for their assistance at I19 beamline (Proposal No. CY22411-1). Thanks are also extended to the "2019 Post-doctoral Junior Leader-Retaining Fellowship, la Caixa Foundation (ID100010434 and fellowship code LCF/BQ/PR19/11700011" and "Subvenciones concedidas a la excelencia cientifica de juniors investigadores, SEJI/2020/034" (J. F.-S.). E.P. acknowledgs the financial support of the European Research Council under the European Union's Horizon 2020 research and innovation programme/ERC Grant Agreement No 814804, MOF-reactors. R. G. thanks ITQ for a contract. E. T. acknowledgs MINECO for a predoctoral grant.
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Type:
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Artículo
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