Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction

Autores
Martínez, José J.; Páez, Luis A.; Gutiérrez, Luisa F.; Pardo Cuervo, Oscar H.; Rojas, Hugo A.; Romanelli, Gustavo Pablo; Portilla, Jaime; Castillo, Juan Carlos; Gamboa Becerra, Diana Paola
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Although different ways of converting 5- (hydroxymethyl)furfural (1) to various substrates with high value have been sought, few transformations have obtained building blocks that can be very useful in the area of fine chemistry. Herein, we report the synthesis of protoanemonin (5-methylenefuran-2(5H)- one) from D-fructose via compound (1), a versatile γalkylidenebutenolide, using an efficient self-catalysed process with formic acid, with high reaction performance and selectivity (up to 94% yield and 98% conversion from (1), while 28% yield from Dfructose). This efficient and simple operational process involved a two-phase aqueous-organic system between chlorinated solvents (CHxCly) and hydrogen peroxide as the initial oxidizing agent. The reaction presents a key cleavage in the 5-hydroxymethyl moiety of (1), due to the Baeyer-Villiger oxidation (BVO) process that generates formic acid in situ. Ultimately, DFF and HMF were successfully obtained in 80% and 98% yield, respectively, starting from D-fructose and using Preyssler heteropolyacids as Brønsted acid catalysts under an atmosphere of oxygen in the absence of hydrogen peroxide.
Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Páez, Luis A.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Gutiérrez, Luisa F.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Pardo Cuervo, Oscar H.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Rojas, Hugo A.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Romanelli, Gustavo Pablo. Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de la Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Portilla, Jaime. Universidad de Los Andes, Colombia; Colombia
Fil: Castillo, Juan Carlos. Universidad Pedagógica y Tecnológica de Colombia; Colombia. Universidad de los Andes; Colombia
Fil: Gamboa Becerra, Diana Paola. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Materia
2,5-FURANDICARBOXALDEHYDE
5-(HYDROXYMETHYL)FURFURAL
BAEYER-VILLIGER OXIDATION
BIOMASS
PROTOANEMONIN
SELF-CATALYSIS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/139754
Acceder
id CONICETDig_e5cdd2a578c2e6b8b56087a2a0a494ec
oai_identifier_str oai:ri.conicet.gov.ar:11336/139754
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reactionMartínez, José J.Páez, Luis A.Gutiérrez, Luisa F.Pardo Cuervo, Oscar H.Rojas, Hugo A.Romanelli, Gustavo PabloPortilla, JaimeCastillo, Juan CarlosGamboa Becerra, Diana Paola2,5-FURANDICARBOXALDEHYDE5-(HYDROXYMETHYL)FURFURALBAEYER-VILLIGER OXIDATIONBIOMASSPROTOANEMONINSELF-CATALYSIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2Although different ways of converting 5- (hydroxymethyl)furfural (1) to various substrates with high value have been sought, few transformations have obtained building blocks that can be very useful in the area of fine chemistry. Herein, we report the synthesis of protoanemonin (5-methylenefuran-2(5H)- one) from D-fructose via compound (1), a versatile γalkylidenebutenolide, using an efficient self-catalysed process with formic acid, with high reaction performance and selectivity (up to 94% yield and 98% conversion from (1), while 28% yield from Dfructose). This efficient and simple operational process involved a two-phase aqueous-organic system between chlorinated solvents (CHxCly) and hydrogen peroxide as the initial oxidizing agent. The reaction presents a key cleavage in the 5-hydroxymethyl moiety of (1), due to the Baeyer-Villiger oxidation (BVO) process that generates formic acid in situ. Ultimately, DFF and HMF were successfully obtained in 80% and 98% yield, respectively, starting from D-fructose and using Preyssler heteropolyacids as Brønsted acid catalysts under an atmosphere of oxygen in the absence of hydrogen peroxide.Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Páez, Luis A.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Gutiérrez, Luisa F.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Pardo Cuervo, Oscar H.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Rojas, Hugo A.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Romanelli, Gustavo Pablo. Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de la Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Portilla, Jaime. Universidad de Los Andes, Colombia; ColombiaFil: Castillo, Juan Carlos. Universidad Pedagógica y Tecnológica de Colombia; Colombia. Universidad de los Andes; ColombiaFil: Gamboa Becerra, Diana Paola. Universidad Pedagógica y Tecnológica de Colombia; ColombiaWiley Blackwell Publishing, Inc2020-09-13info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/139754Martínez, José J.; Páez, Luis A.; Gutiérrez, Luisa F.; Pardo Cuervo, Oscar H.; Rojas, Hugo A.; et al.; Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction; Wiley Blackwell Publishing, Inc; Asian Journal of Organic Chemistry; 9; 12; 13-9-2020; 2184-21902193-5807CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202000406info:eu-repo/semantics/altIdentifier/doi/10.1002/ajoc.202000406info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:09Zoai:ri.conicet.gov.ar:11336/139754instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:33:10.259CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
title Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
spellingShingle Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
Martínez, José J.
2,5-FURANDICARBOXALDEHYDE
5-(HYDROXYMETHYL)FURFURAL
BAEYER-VILLIGER OXIDATION
BIOMASS
PROTOANEMONIN
SELF-CATALYSIS
title_short Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
title_full Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
title_fullStr Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
title_full_unstemmed Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
title_sort Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction
dc.creator.none.fl_str_mv Martínez, José J.
Páez, Luis A.
Gutiérrez, Luisa F.
Pardo Cuervo, Oscar H.
Rojas, Hugo A.
Romanelli, Gustavo Pablo
Portilla, Jaime
Castillo, Juan Carlos
Gamboa Becerra, Diana Paola
author Martínez, José J.
author_facet Martínez, José J.
Páez, Luis A.
Gutiérrez, Luisa F.
Pardo Cuervo, Oscar H.
Rojas, Hugo A.
Romanelli, Gustavo Pablo
Portilla, Jaime
Castillo, Juan Carlos
Gamboa Becerra, Diana Paola
author_role author
author2 Páez, Luis A.
Gutiérrez, Luisa F.
Pardo Cuervo, Oscar H.
Rojas, Hugo A.
Romanelli, Gustavo Pablo
Portilla, Jaime
Castillo, Juan Carlos
Gamboa Becerra, Diana Paola
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 2,5-FURANDICARBOXALDEHYDE
5-(HYDROXYMETHYL)FURFURAL
BAEYER-VILLIGER OXIDATION
BIOMASS
PROTOANEMONIN
SELF-CATALYSIS
topic 2,5-FURANDICARBOXALDEHYDE
5-(HYDROXYMETHYL)FURFURAL
BAEYER-VILLIGER OXIDATION
BIOMASS
PROTOANEMONIN
SELF-CATALYSIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Although different ways of converting 5- (hydroxymethyl)furfural (1) to various substrates with high value have been sought, few transformations have obtained building blocks that can be very useful in the area of fine chemistry. Herein, we report the synthesis of protoanemonin (5-methylenefuran-2(5H)- one) from D-fructose via compound (1), a versatile γalkylidenebutenolide, using an efficient self-catalysed process with formic acid, with high reaction performance and selectivity (up to 94% yield and 98% conversion from (1), while 28% yield from Dfructose). This efficient and simple operational process involved a two-phase aqueous-organic system between chlorinated solvents (CHxCly) and hydrogen peroxide as the initial oxidizing agent. The reaction presents a key cleavage in the 5-hydroxymethyl moiety of (1), due to the Baeyer-Villiger oxidation (BVO) process that generates formic acid in situ. Ultimately, DFF and HMF were successfully obtained in 80% and 98% yield, respectively, starting from D-fructose and using Preyssler heteropolyacids as Brønsted acid catalysts under an atmosphere of oxygen in the absence of hydrogen peroxide.
Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Páez, Luis A.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Gutiérrez, Luisa F.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Pardo Cuervo, Oscar H.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Rojas, Hugo A.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Romanelli, Gustavo Pablo. Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de la Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Portilla, Jaime. Universidad de Los Andes, Colombia; Colombia
Fil: Castillo, Juan Carlos. Universidad Pedagógica y Tecnológica de Colombia; Colombia. Universidad de los Andes; Colombia
Fil: Gamboa Becerra, Diana Paola. Universidad Pedagógica y Tecnológica de Colombia; Colombia
description Although different ways of converting 5- (hydroxymethyl)furfural (1) to various substrates with high value have been sought, few transformations have obtained building blocks that can be very useful in the area of fine chemistry. Herein, we report the synthesis of protoanemonin (5-methylenefuran-2(5H)- one) from D-fructose via compound (1), a versatile γalkylidenebutenolide, using an efficient self-catalysed process with formic acid, with high reaction performance and selectivity (up to 94% yield and 98% conversion from (1), while 28% yield from Dfructose). This efficient and simple operational process involved a two-phase aqueous-organic system between chlorinated solvents (CHxCly) and hydrogen peroxide as the initial oxidizing agent. The reaction presents a key cleavage in the 5-hydroxymethyl moiety of (1), due to the Baeyer-Villiger oxidation (BVO) process that generates formic acid in situ. Ultimately, DFF and HMF were successfully obtained in 80% and 98% yield, respectively, starting from D-fructose and using Preyssler heteropolyacids as Brønsted acid catalysts under an atmosphere of oxygen in the absence of hydrogen peroxide.
publishDate 2020
dc.date.none.fl_str_mv 2020-09-13
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/139754
Martínez, José J.; Páez, Luis A.; Gutiérrez, Luisa F.; Pardo Cuervo, Oscar H.; Rojas, Hugo A.; et al.; Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction; Wiley Blackwell Publishing, Inc; Asian Journal of Organic Chemistry; 9; 12; 13-9-2020; 2184-2190
2193-5807
CONICET Digital
CONICET
url http://hdl.handle.net/11336/139754
identifier_str_mv Martínez, José J.; Páez, Luis A.; Gutiérrez, Luisa F.; Pardo Cuervo, Oscar H.; Rojas, Hugo A.; et al.; Obtaining protoanemonin through selective oxidation of Dfructose and 5-(hydroxymethyl) furfural in a self-catalysed reaction; Wiley Blackwell Publishing, Inc; Asian Journal of Organic Chemistry; 9; 12; 13-9-2020; 2184-2190
2193-5807
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202000406
info:eu-repo/semantics/altIdentifier/doi/10.1002/ajoc.202000406
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844614346717528064
score 13.069144

Publicaciones similares