Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step

Autores
Postigo, Jose Alberto; Kopsov, Sergey; Zlotsky, Simon S.; Ferreri, Carla; Chatgilialoglu, Chryssostomos
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The classical radical-based hydrosilylation reaction of organic compounds bearing C-C multiple bonds is usually carried out in organic solvents and is herein presented in water with both organic solventsoluble and water-soluble substrates. Different initiation methods to accomplish the radical-induced hydrosilylation reaction of C-C multiple bonds in water with (Me 3Si)3SiH are presented. In the thermal decomposition of azo compounds, the system comprising substrate, silane, and azo-initiator (ACCN) mixed in aqueous medium at 100 °C worked well for both hydrophilic and hydrophobic substrates, with the only variation that the amphiphilic thiol HOCH2CH3SH was also needed in the case of the watersoluble compounds. Dioxygen initiation is shown to afford excellent yields of hydrosilylated products derived from substrates bearing C-C triple bonds and moderate to low yields of hydrosilylated products derived from C-C double-bonded compounds in water. Photochemical initiation in the absence of a chemical radical precursor other than the silane is also found to be a very efficient and convenient method to induce the hydrosilylation reaction of both C-C double and triple bonds of organic compounds (hydrophilic and hydrophobic substrates) with (Me3Si)3SiH in water. These three alternative radicalbased methodologies studied in water are confronted.
Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consiglio Nazionale delle Ricerche; Italia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Kopsov, Sergey. Consiglio Nazionale delle Ricerche; Italia
Fil: Zlotsky, Simon S.. Ufa State Petroleum Technological University; Rusia
Fil: Ferreri, Carla. Consiglio Nazionale delle Ricerche; Italia
Fil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; Italia
Materia
radical reactions
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:11336/114263
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation stepPostigo, Jose AlbertoKopsov, SergeyZlotsky, Simon S.Ferreri, CarlaChatgilialoglu, Chryssostomosradical reactionshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The classical radical-based hydrosilylation reaction of organic compounds bearing C-C multiple bonds is usually carried out in organic solvents and is herein presented in water with both organic solventsoluble and water-soluble substrates. Different initiation methods to accomplish the radical-induced hydrosilylation reaction of C-C multiple bonds in water with (Me 3Si)3SiH are presented. In the thermal decomposition of azo compounds, the system comprising substrate, silane, and azo-initiator (ACCN) mixed in aqueous medium at 100 °C worked well for both hydrophilic and hydrophobic substrates, with the only variation that the amphiphilic thiol HOCH2CH3SH was also needed in the case of the watersoluble compounds. Dioxygen initiation is shown to afford excellent yields of hydrosilylated products derived from substrates bearing C-C triple bonds and moderate to low yields of hydrosilylated products derived from C-C double-bonded compounds in water. Photochemical initiation in the absence of a chemical radical precursor other than the silane is also found to be a very efficient and convenient method to induce the hydrosilylation reaction of both C-C double and triple bonds of organic compounds (hydrophilic and hydrophobic substrates) with (Me3Si)3SiH in water. These three alternative radicalbased methodologies studied in water are confronted.Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consiglio Nazionale delle Ricerche; Italia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Kopsov, Sergey. Consiglio Nazionale delle Ricerche; ItaliaFil: Zlotsky, Simon S.. Ufa State Petroleum Technological University; RusiaFil: Ferreri, Carla. Consiglio Nazionale delle Ricerche; ItaliaFil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; ItaliaAmerican Chemical Society2009-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/114263Postigo, Jose Alberto; Kopsov, Sergey; Zlotsky, Simon S.; Ferreri, Carla; Chatgilialoglu, Chryssostomos; Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step; American Chemical Society; Organometallics; 28; 11; 6-2009; 3282-32870276-7333CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/om900086minfo:eu-repo/semantics/altIdentifier/doi/10.1021/om900086minfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-29T12:00:53Zoai:ri.conicet.gov.ar:11336/114263instacron: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:34982025-10-29 12:00:53.447CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
title Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
spellingShingle Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
Postigo, Jose Alberto
radical reactions
title_short Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
title_full Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
title_fullStr Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
title_full_unstemmed Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
title_sort Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step
dc.creator.none.fl_str_mv Postigo, Jose Alberto
Kopsov, Sergey
Zlotsky, Simon S.
Ferreri, Carla
Chatgilialoglu, Chryssostomos
author Postigo, Jose Alberto
author_facet Postigo, Jose Alberto
Kopsov, Sergey
Zlotsky, Simon S.
Ferreri, Carla
Chatgilialoglu, Chryssostomos
author_role author
author2 Kopsov, Sergey
Zlotsky, Simon S.
Ferreri, Carla
Chatgilialoglu, Chryssostomos
author2_role author
author
author
author
dc.subject.none.fl_str_mv radical reactions
topic radical reactions
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 classical radical-based hydrosilylation reaction of organic compounds bearing C-C multiple bonds is usually carried out in organic solvents and is herein presented in water with both organic solventsoluble and water-soluble substrates. Different initiation methods to accomplish the radical-induced hydrosilylation reaction of C-C multiple bonds in water with (Me 3Si)3SiH are presented. In the thermal decomposition of azo compounds, the system comprising substrate, silane, and azo-initiator (ACCN) mixed in aqueous medium at 100 °C worked well for both hydrophilic and hydrophobic substrates, with the only variation that the amphiphilic thiol HOCH2CH3SH was also needed in the case of the watersoluble compounds. Dioxygen initiation is shown to afford excellent yields of hydrosilylated products derived from substrates bearing C-C triple bonds and moderate to low yields of hydrosilylated products derived from C-C double-bonded compounds in water. Photochemical initiation in the absence of a chemical radical precursor other than the silane is also found to be a very efficient and convenient method to induce the hydrosilylation reaction of both C-C double and triple bonds of organic compounds (hydrophilic and hydrophobic substrates) with (Me3Si)3SiH in water. These three alternative radicalbased methodologies studied in water are confronted.
Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consiglio Nazionale delle Ricerche; Italia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Kopsov, Sergey. Consiglio Nazionale delle Ricerche; Italia
Fil: Zlotsky, Simon S.. Ufa State Petroleum Technological University; Rusia
Fil: Ferreri, Carla. Consiglio Nazionale delle Ricerche; Italia
Fil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; Italia
description The classical radical-based hydrosilylation reaction of organic compounds bearing C-C multiple bonds is usually carried out in organic solvents and is herein presented in water with both organic solventsoluble and water-soluble substrates. Different initiation methods to accomplish the radical-induced hydrosilylation reaction of C-C multiple bonds in water with (Me 3Si)3SiH are presented. In the thermal decomposition of azo compounds, the system comprising substrate, silane, and azo-initiator (ACCN) mixed in aqueous medium at 100 °C worked well for both hydrophilic and hydrophobic substrates, with the only variation that the amphiphilic thiol HOCH2CH3SH was also needed in the case of the watersoluble compounds. Dioxygen initiation is shown to afford excellent yields of hydrosilylated products derived from substrates bearing C-C triple bonds and moderate to low yields of hydrosilylated products derived from C-C double-bonded compounds in water. Photochemical initiation in the absence of a chemical radical precursor other than the silane is also found to be a very efficient and convenient method to induce the hydrosilylation reaction of both C-C double and triple bonds of organic compounds (hydrophilic and hydrophobic substrates) with (Me3Si)3SiH in water. These three alternative radicalbased methodologies studied in water are confronted.
publishDate 2009
dc.date.none.fl_str_mv 2009-06
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/11336/114263
Postigo, Jose Alberto; Kopsov, Sergey; Zlotsky, Simon S.; Ferreri, Carla; Chatgilialoglu, Chryssostomos; Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step; American Chemical Society; Organometallics; 28; 11; 6-2009; 3282-3287
0276-7333
CONICET Digital
CONICET
url http://hdl.handle.net/11336/114263
identifier_str_mv Postigo, Jose Alberto; Kopsov, Sergey; Zlotsky, Simon S.; Ferreri, Carla; Chatgilialoglu, Chryssostomos; Hydrosilylation of C-C multiple bonds using (Me3Si) 3SiH in water: Comparative study of the radical initiation step; American Chemical Society; Organometallics; 28; 11; 6-2009; 3282-3287
0276-7333
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.acs.org/doi/abs/10.1021/om900086m
info:eu-repo/semantics/altIdentifier/doi/10.1021/om900086m
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_ 1847426760259403776
score 13.10058

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