Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions

Autores
Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.
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
Vinyl Selenides
Ksecn
Transition Metal Free
Stereoselectivity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/47495
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditionsHeredia, Adrián AlbertoPeñeñory, Alicia BeatrizVinyl SelenidesKsecnTransition Metal FreeStereoselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.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; ArgentinaRoyal Society of Chemistry2015-12-09info: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/11336/47495Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions; Royal Society of Chemistry; RSC Advances; 5; 9-12-2015; 105699-1057062046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C5RA20883Ainfo:eu-repo/semantics/altIdentifier/doi/10.1039/c5ra20883ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:18:22Zoai:ri.conicet.gov.ar:11336/47495instacron: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:34982025-10-22 12:18:22.62CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
title Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
spellingShingle Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
Heredia, Adrián Alberto
Vinyl Selenides
Ksecn
Transition Metal Free
Stereoselectivity
title_short Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
title_full Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
title_fullStr Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
title_full_unstemmed Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
title_sort Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
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 Vinyl Selenides
Ksecn
Transition Metal Free
Stereoselectivity
topic Vinyl Selenides
Ksecn
Transition Metal Free
Stereoselectivity
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 simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.
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 simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.
publishDate 2015
dc.date.none.fl_str_mv 2015-12-09
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/11336/47495
Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions; Royal Society of Chemistry; RSC Advances; 5; 9-12-2015; 105699-105706
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47495
identifier_str_mv Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions; Royal Society of Chemistry; RSC Advances; 5; 9-12-2015; 105699-105706
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C5RA20883A
info:eu-repo/semantics/altIdentifier/doi/10.1039/c5ra20883a
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 12.982451

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