One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols

Autores
Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols.
Fil: Heredia, Adrián Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
Sulfuros de Vinilo
Tioacetato de Potasio
Métodos Sintéticos
Halo Estirilos
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:11336/22112
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and ThiolsHeredia, Adrián AlbertoPeñeñory, Alicia BeatrizSulfuros de ViniloTioacetato de PotasioMétodos SintéticosHalo Estiriloshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols.Fil: Heredia, Adrián Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaWiley VCH Verlag2012-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/22112Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols; Wiley VCH Verlag; European Journal of Organic Chemistry; 2013; 5; 12-2012; 991-9971434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201201163info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201163/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:54:35Zoai:ri.conicet.gov.ar:11336/22112instacron: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 09:54:35.349CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
title One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
spellingShingle One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
Heredia, Adrián Alberto
Sulfuros de Vinilo
Tioacetato de Potasio
Métodos Sintéticos
Halo Estirilos
title_short One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
title_full One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
title_fullStr One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
title_full_unstemmed One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
title_sort One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
dc.creator.none.fl_str_mv Heredia, Adrián Alberto
Peñeñory, Alicia Beatriz
author Heredia, Adrián Alberto
author_facet Heredia, Adrián Alberto
Peñeñory, Alicia Beatriz
author_role author
author2 Peñeñory, Alicia Beatriz
author2_role author
dc.subject.none.fl_str_mv Sulfuros de Vinilo
Tioacetato de Potasio
Métodos Sintéticos
Halo Estirilos
topic Sulfuros de Vinilo
Tioacetato de Potasio
Métodos Sintéticos
Halo Estirilos
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols.
Fil: Heredia, Adrián Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols.
publishDate 2012
dc.date.none.fl_str_mv 2012-12
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/11336/22112
Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols; Wiley VCH Verlag; European Journal of Organic Chemistry; 2013; 5; 12-2012; 991-997
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/22112
identifier_str_mv Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols; Wiley VCH Verlag; European Journal of Organic Chemistry; 2013; 5; 12-2012; 991-997
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201201163
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201163/abstract
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
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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_ 1844613657055461376
score 13.070432

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