Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry

Autores
Lafuente, María Leticia; Díaz, Gisela; Bravo, Rodolfo Daniel; Ponzinibbio, Agustín
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Background: The ionic liquid triethylammonium acetate (TEAA) was found to be an efficient solvent in the acetylation of alcohols, amines, oximes and thiols to their corresponding acetyl compounds using only a 10% excess of acetic anhydride under mild conditions. Moreover TEAA is not only an inexpensive and recyclable solvent but also an anomeric selective catalyst in the per-O-acetylation of sugar moieties. Methods: Simple and effective organic synthesis protocols were provided for the selective acetylation of several substrates. The products were fully characterized by 1H and 13C NMR spectroscopy and the anomeric ratios were obtained from the 1H spectra. Results: Structurally diverse alcohols, phenols, thiols, amines, carbohydrates and oximes underwent acylation under mild conditions by this procedure to provide the corresponding acetates in excellent yields. TEAA ionic liquid is unique in its capability to act as both, solvent and high selective catalyst. As expected, the reaction proceeds with high b anomeric selectivity for sugars derivatives. Moreover, the ionic liquid was regenerated, recycled and reused for three times without apparent loss of reactivity and selectivity in all cases. Conclusions: The present procedure provides a powerful and versatile acylation method for alcohols, phenols, thiols, amines, oximes and carbohydrates. This protocol is endowed with several unique merits: selectivity, cost-efficiency, atom-economy and mild reaction conditions tolerable to acid sensitive functionalities. With these features, this method may be considered as a better alternative for the acetylation of a wide range of substrates.
Fil: Lafuente, María Leticia. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Díaz, Gisela. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Bravo, Rodolfo Daniel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Ponzinibbio, Agustín. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Acylation
Carbohydrates
Green Chemistry
Triethylammonium Acetate (Teaa)
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:11336/54615
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistryLafuente, María LeticiaDíaz, GiselaBravo, Rodolfo DanielPonzinibbio, AgustínAcylationCarbohydratesGreen ChemistryTriethylammonium Acetate (Teaa)https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Background: The ionic liquid triethylammonium acetate (TEAA) was found to be an efficient solvent in the acetylation of alcohols, amines, oximes and thiols to their corresponding acetyl compounds using only a 10% excess of acetic anhydride under mild conditions. Moreover TEAA is not only an inexpensive and recyclable solvent but also an anomeric selective catalyst in the per-O-acetylation of sugar moieties. Methods: Simple and effective organic synthesis protocols were provided for the selective acetylation of several substrates. The products were fully characterized by 1H and 13C NMR spectroscopy and the anomeric ratios were obtained from the 1H spectra. Results: Structurally diverse alcohols, phenols, thiols, amines, carbohydrates and oximes underwent acylation under mild conditions by this procedure to provide the corresponding acetates in excellent yields. TEAA ionic liquid is unique in its capability to act as both, solvent and high selective catalyst. As expected, the reaction proceeds with high b anomeric selectivity for sugars derivatives. Moreover, the ionic liquid was regenerated, recycled and reused for three times without apparent loss of reactivity and selectivity in all cases. Conclusions: The present procedure provides a powerful and versatile acylation method for alcohols, phenols, thiols, amines, oximes and carbohydrates. This protocol is endowed with several unique merits: selectivity, cost-efficiency, atom-economy and mild reaction conditions tolerable to acid sensitive functionalities. With these features, this method may be considered as a better alternative for the acetylation of a wide range of substrates.Fil: Lafuente, María Leticia. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Díaz, Gisela. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Bravo, Rodolfo Daniel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Ponzinibbio, Agustín. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaBentham Science Publishers2016-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/54615Lafuente, María Leticia; Díaz, Gisela; Bravo, Rodolfo Daniel; Ponzinibbio, Agustín; Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry; Bentham Science Publishers; Letters in Organic Chemistry; 13; 3; 3-2016; 195-2001570-1786CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.2174/1570178613666160104233129info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/138291info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:58Zoai:ri.conicet.gov.ar:11336/54615instacron: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 09:39:59.169CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
title Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
spellingShingle Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
Lafuente, María Leticia
Acylation
Carbohydrates
Green Chemistry
Triethylammonium Acetate (Teaa)
title_short Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
title_full Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
title_fullStr Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
title_full_unstemmed Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
title_sort Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry
dc.creator.none.fl_str_mv Lafuente, María Leticia
Díaz, Gisela
Bravo, Rodolfo Daniel
Ponzinibbio, Agustín
author Lafuente, María Leticia
author_facet Lafuente, María Leticia
Díaz, Gisela
Bravo, Rodolfo Daniel
Ponzinibbio, Agustín
author_role author
author2 Díaz, Gisela
Bravo, Rodolfo Daniel
Ponzinibbio, Agustín
author2_role author
author
author
dc.subject.none.fl_str_mv Acylation
Carbohydrates
Green Chemistry
Triethylammonium Acetate (Teaa)
topic Acylation
Carbohydrates
Green Chemistry
Triethylammonium Acetate (Teaa)
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Background: The ionic liquid triethylammonium acetate (TEAA) was found to be an efficient solvent in the acetylation of alcohols, amines, oximes and thiols to their corresponding acetyl compounds using only a 10% excess of acetic anhydride under mild conditions. Moreover TEAA is not only an inexpensive and recyclable solvent but also an anomeric selective catalyst in the per-O-acetylation of sugar moieties. Methods: Simple and effective organic synthesis protocols were provided for the selective acetylation of several substrates. The products were fully characterized by 1H and 13C NMR spectroscopy and the anomeric ratios were obtained from the 1H spectra. Results: Structurally diverse alcohols, phenols, thiols, amines, carbohydrates and oximes underwent acylation under mild conditions by this procedure to provide the corresponding acetates in excellent yields. TEAA ionic liquid is unique in its capability to act as both, solvent and high selective catalyst. As expected, the reaction proceeds with high b anomeric selectivity for sugars derivatives. Moreover, the ionic liquid was regenerated, recycled and reused for three times without apparent loss of reactivity and selectivity in all cases. Conclusions: The present procedure provides a powerful and versatile acylation method for alcohols, phenols, thiols, amines, oximes and carbohydrates. This protocol is endowed with several unique merits: selectivity, cost-efficiency, atom-economy and mild reaction conditions tolerable to acid sensitive functionalities. With these features, this method may be considered as a better alternative for the acetylation of a wide range of substrates.
Fil: Lafuente, María Leticia. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Díaz, Gisela. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Bravo, Rodolfo Daniel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Ponzinibbio, Agustín. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description Background: The ionic liquid triethylammonium acetate (TEAA) was found to be an efficient solvent in the acetylation of alcohols, amines, oximes and thiols to their corresponding acetyl compounds using only a 10% excess of acetic anhydride under mild conditions. Moreover TEAA is not only an inexpensive and recyclable solvent but also an anomeric selective catalyst in the per-O-acetylation of sugar moieties. Methods: Simple and effective organic synthesis protocols were provided for the selective acetylation of several substrates. The products were fully characterized by 1H and 13C NMR spectroscopy and the anomeric ratios were obtained from the 1H spectra. Results: Structurally diverse alcohols, phenols, thiols, amines, carbohydrates and oximes underwent acylation under mild conditions by this procedure to provide the corresponding acetates in excellent yields. TEAA ionic liquid is unique in its capability to act as both, solvent and high selective catalyst. As expected, the reaction proceeds with high b anomeric selectivity for sugars derivatives. Moreover, the ionic liquid was regenerated, recycled and reused for three times without apparent loss of reactivity and selectivity in all cases. Conclusions: The present procedure provides a powerful and versatile acylation method for alcohols, phenols, thiols, amines, oximes and carbohydrates. This protocol is endowed with several unique merits: selectivity, cost-efficiency, atom-economy and mild reaction conditions tolerable to acid sensitive functionalities. With these features, this method may be considered as a better alternative for the acetylation of a wide range of substrates.
publishDate 2016
dc.date.none.fl_str_mv 2016-03
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/11336/54615
Lafuente, María Leticia; Díaz, Gisela; Bravo, Rodolfo Daniel; Ponzinibbio, Agustín; Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry; Bentham Science Publishers; Letters in Organic Chemistry; 13; 3; 3-2016; 195-200
1570-1786
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54615
identifier_str_mv Lafuente, María Leticia; Díaz, Gisela; Bravo, Rodolfo Daniel; Ponzinibbio, Agustín; Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry; Bentham Science Publishers; Letters in Organic Chemistry; 13; 3; 3-2016; 195-200
1570-1786
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.2174/1570178613666160104233129
info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/138291
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
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
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score 13.070432

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