Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water

Autores
Barata Vallejo, Sebastian; Ferreri, Carla; Golding, Bernard T.; Chatgilialoglu, Chryssostomos
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Hydrogen sulfide (H2S) was evaluated for its peculiar sulfur radical species generated at different pHs and was used under photolytical conditions in aqueous medium for the reduction of 1,2-diols to alcohols. The conversion steps of 1,2-cyclopentanediol to cyclopentanol via cyclopentanone were analyzed, and it was proven that the reaction proceeds via a dual catalytic/radical chain mechanism. This approach was successfully adapted to the reduction of a variety of carbonyl compounds using H2S at pH 9 in water. This work opens up the field of environmental friendly synthetic processes using the pH-driven modulation of reactivity of this simple reagent in water.
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Consiglio Nazionale delle Ricerche; Italia
Fil: Ferreri, Carla. Consiglio Nazionale delle Ricerche; Italia
Fil: Golding, Bernard T.. University of Newcastle; Reino Unido
Fil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; Italia
Materia
Carbonyl Reduction in Water
1,2-Diol Mono-deoxygenation
Hydrogen Sulfide
Radical Reduction
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:11336/98869
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/98869
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in WaterBarata Vallejo, SebastianFerreri, CarlaGolding, Bernard T.Chatgilialoglu, ChryssostomosCarbonyl Reduction in Water1,2-Diol Mono-deoxygenationHydrogen SulfideRadical Reductionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Hydrogen sulfide (H2S) was evaluated for its peculiar sulfur radical species generated at different pHs and was used under photolytical conditions in aqueous medium for the reduction of 1,2-diols to alcohols. The conversion steps of 1,2-cyclopentanediol to cyclopentanol via cyclopentanone were analyzed, and it was proven that the reaction proceeds via a dual catalytic/radical chain mechanism. This approach was successfully adapted to the reduction of a variety of carbonyl compounds using H2S at pH 9 in water. This work opens up the field of environmental friendly synthetic processes using the pH-driven modulation of reactivity of this simple reagent in water.Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Consiglio Nazionale delle Ricerche; ItaliaFil: Ferreri, Carla. Consiglio Nazionale delle Ricerche; ItaliaFil: Golding, Bernard T.. University of Newcastle; Reino UnidoFil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; ItaliaAmerican Chemical Society2018-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/98869Barata Vallejo, Sebastian; Ferreri, Carla; Golding, Bernard T.; Chatgilialoglu, Chryssostomos; Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water; American Chemical Society; Organic Letters; 20; 14; 7-2018; 4290-42941523-7060CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.orglett.8b01713info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.orglett.8b01713info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:27:25Zoai:ri.conicet.gov.ar:11336/98869instacron: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:34982025-10-15 14:27:26.242CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
title Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
spellingShingle Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
Barata Vallejo, Sebastian
Carbonyl Reduction in Water
1,2-Diol Mono-deoxygenation
Hydrogen Sulfide
Radical Reduction
title_short Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
title_full Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
title_fullStr Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
title_full_unstemmed Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
title_sort Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
dc.creator.none.fl_str_mv Barata Vallejo, Sebastian
Ferreri, Carla
Golding, Bernard T.
Chatgilialoglu, Chryssostomos
author Barata Vallejo, Sebastian
author_facet Barata Vallejo, Sebastian
Ferreri, Carla
Golding, Bernard T.
Chatgilialoglu, Chryssostomos
author_role author
author2 Ferreri, Carla
Golding, Bernard T.
Chatgilialoglu, Chryssostomos
author2_role author
author
author
dc.subject.none.fl_str_mv Carbonyl Reduction in Water
1,2-Diol Mono-deoxygenation
Hydrogen Sulfide
Radical Reduction
topic Carbonyl Reduction in Water
1,2-Diol Mono-deoxygenation
Hydrogen Sulfide
Radical Reduction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Hydrogen sulfide (H2S) was evaluated for its peculiar sulfur radical species generated at different pHs and was used under photolytical conditions in aqueous medium for the reduction of 1,2-diols to alcohols. The conversion steps of 1,2-cyclopentanediol to cyclopentanol via cyclopentanone were analyzed, and it was proven that the reaction proceeds via a dual catalytic/radical chain mechanism. This approach was successfully adapted to the reduction of a variety of carbonyl compounds using H2S at pH 9 in water. This work opens up the field of environmental friendly synthetic processes using the pH-driven modulation of reactivity of this simple reagent in water.
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Consiglio Nazionale delle Ricerche; Italia
Fil: Ferreri, Carla. Consiglio Nazionale delle Ricerche; Italia
Fil: Golding, Bernard T.. University of Newcastle; Reino Unido
Fil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; Italia
description Hydrogen sulfide (H2S) was evaluated for its peculiar sulfur radical species generated at different pHs and was used under photolytical conditions in aqueous medium for the reduction of 1,2-diols to alcohols. The conversion steps of 1,2-cyclopentanediol to cyclopentanol via cyclopentanone were analyzed, and it was proven that the reaction proceeds via a dual catalytic/radical chain mechanism. This approach was successfully adapted to the reduction of a variety of carbonyl compounds using H2S at pH 9 in water. This work opens up the field of environmental friendly synthetic processes using the pH-driven modulation of reactivity of this simple reagent in water.
publishDate 2018
dc.date.none.fl_str_mv 2018-07
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/11336/98869
Barata Vallejo, Sebastian; Ferreri, Carla; Golding, Bernard T.; Chatgilialoglu, Chryssostomos; Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water; American Chemical Society; Organic Letters; 20; 14; 7-2018; 4290-4294
1523-7060
CONICET Digital
CONICET
url http://hdl.handle.net/11336/98869
identifier_str_mv Barata Vallejo, Sebastian; Ferreri, Carla; Golding, Bernard T.; Chatgilialoglu, Chryssostomos; Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water; American Chemical Society; Organic Letters; 20; 14; 7-2018; 4290-4294
1523-7060
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.orglett.8b01713
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.orglett.8b01713
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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_ 1846082729444114432
score 13.22299

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