Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes

Autores
Moglie, Yanina Fernanda; González Soria, María José; Martín García, Iris; Radivoy, Gabriel Eduardo; Alonso, Francisco
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.
Fil: Moglie, Yanina Fernanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: González Soria, María José. Universidad de Alicante, Alicante; España
Fil: Martín García, Iris. Universidad de Alicante, Alicante; España
Fil: Radivoy, Gabriel Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Alonso, Francisco. Universidad de Alicante, Alicante; España
Materia
ALKENE HYDROPHOSPINATION
ALKYNE HYDROPHOSPHINATION
CATALYST FREE
SOLVENT FREE
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:11336/54585
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynesMoglie, Yanina FernandaGonzález Soria, María JoséMartín García, IrisRadivoy, Gabriel EduardoAlonso, FranciscoALKENE HYDROPHOSPINATIONALKYNE HYDROPHOSPHINATIONCATALYST FREESOLVENT FREEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.Fil: Moglie, Yanina Fernanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: González Soria, María José. Universidad de Alicante, Alicante; EspañaFil: Martín García, Iris. Universidad de Alicante, Alicante; EspañaFil: Radivoy, Gabriel Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Alonso, Francisco. Universidad de Alicante, Alicante; EspañaRoyal Society of Chemistry2016-05-26info: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/11336/54585Moglie, Yanina Fernanda; González Soria, María José; Martín García, Iris; Radivoy, Gabriel Eduardo; Alonso, Francisco; Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes; Royal Society of Chemistry; Green Chemistry (print); 18; 18; 26-5-2016; 4896-49071463-9262CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2016/gc/c6gc00903d#!divAbstracinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C6GC00903Dinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:07:53Zoai:ri.conicet.gov.ar:11336/54585instacron: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:34982025-09-03 10:07:54.159CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
title Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
spellingShingle Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
Moglie, Yanina Fernanda
ALKENE HYDROPHOSPINATION
ALKYNE HYDROPHOSPHINATION
CATALYST FREE
SOLVENT FREE
title_short Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
title_full Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
title_fullStr Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
title_full_unstemmed Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
title_sort Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
dc.creator.none.fl_str_mv Moglie, Yanina Fernanda
González Soria, María José
Martín García, Iris
Radivoy, Gabriel Eduardo
Alonso, Francisco
author Moglie, Yanina Fernanda
author_facet Moglie, Yanina Fernanda
González Soria, María José
Martín García, Iris
Radivoy, Gabriel Eduardo
Alonso, Francisco
author_role author
author2 González Soria, María José
Martín García, Iris
Radivoy, Gabriel Eduardo
Alonso, Francisco
author2_role author
author
author
author
dc.subject.none.fl_str_mv ALKENE HYDROPHOSPINATION
ALKYNE HYDROPHOSPHINATION
CATALYST FREE
SOLVENT FREE
topic ALKENE HYDROPHOSPINATION
ALKYNE HYDROPHOSPHINATION
CATALYST FREE
SOLVENT FREE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.
Fil: Moglie, Yanina Fernanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: González Soria, María José. Universidad de Alicante, Alicante; España
Fil: Martín García, Iris. Universidad de Alicante, Alicante; España
Fil: Radivoy, Gabriel Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Alonso, Francisco. Universidad de Alicante, Alicante; España
description The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.
publishDate 2016
dc.date.none.fl_str_mv 2016-05-26
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/11336/54585
Moglie, Yanina Fernanda; González Soria, María José; Martín García, Iris; Radivoy, Gabriel Eduardo; Alonso, Francisco; Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes; Royal Society of Chemistry; Green Chemistry (print); 18; 18; 26-5-2016; 4896-4907
1463-9262
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54585
identifier_str_mv Moglie, Yanina Fernanda; González Soria, María José; Martín García, Iris; Radivoy, Gabriel Eduardo; Alonso, Francisco; Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes; Royal Society of Chemistry; Green Chemistry (print); 18; 18; 26-5-2016; 4896-4907
1463-9262
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://pubs.rsc.org/en/content/articlelanding/2016/gc/c6gc00903d#!divAbstrac
info:eu-repo/semantics/altIdentifier/doi/10.1039/C6GC00903D
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
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
_version_ 1842270022623297536
score 13.13397

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