Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation

Autores
Postigo, Jose Alberto; Sbarbati Nudelman, Norma
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The relevance of radical initiation metodologies for the classical hydrosilylation reactions of organic compounds bearing C[BOND]C multiple bonds is due to the need to come up with newer and more effcient methods to effect this reaction, on account of its applications on surface chemistry. In the past, when organic solvents were employed, thermal and photochemical methods for the chain initiation reaction have been documented (thermal and photochemical decomposition of azo compounds). We herein present the dioxygen-initiation technique of the classical radical hydrosilylation reaction of C[BOND]C triple bonds with tris(trimethylsilyl)silane ((Me3Si)3SiH) in water. This initiation technique is confronted with the photochemical radical initiation in the absence of a chemical radical precursor other than the silane and also confronted with the classical thermal initiation triggered by the decomposition of an azo compound, both performed in water. The radical-based dioxygen initiation methodology studied in water is shown to afford the highest Z:E stereoselective ratios of hydrosilylated alkenes.
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Belgrano; Argentina
Fil: Sbarbati Nudelman, Norma. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Materia
Dioxygen Initiation
Hydrosilylation
Radical Reactions in Water
Reaction Mechanism
Tri(Trimethylsilyl)Silane
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:11336/14269
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/14269
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiationPostigo, Jose AlbertoSbarbati Nudelman, NormaDioxygen InitiationHydrosilylationRadical Reactions in WaterReaction MechanismTri(Trimethylsilyl)Silanehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The relevance of radical initiation metodologies for the classical hydrosilylation reactions of organic compounds bearing C[BOND]C multiple bonds is due to the need to come up with newer and more effcient methods to effect this reaction, on account of its applications on surface chemistry. In the past, when organic solvents were employed, thermal and photochemical methods for the chain initiation reaction have been documented (thermal and photochemical decomposition of azo compounds). We herein present the dioxygen-initiation technique of the classical radical hydrosilylation reaction of C[BOND]C triple bonds with tris(trimethylsilyl)silane ((Me3Si)3SiH) in water. This initiation technique is confronted with the photochemical radical initiation in the absence of a chemical radical precursor other than the silane and also confronted with the classical thermal initiation triggered by the decomposition of an azo compound, both performed in water. The radical-based dioxygen initiation methodology studied in water is shown to afford the highest Z:E stereoselective ratios of hydrosilylated alkenes.Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Belgrano; ArgentinaFil: Sbarbati Nudelman, Norma. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaWiley2010-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/14269Postigo, Jose Alberto; Sbarbati Nudelman, Norma; Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation; Wiley; Journal Of Physical Organic Chemistry; 23; 10; 10-2010; 910-9140894-32301099-1395enginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/poc.1703/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.1703info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-29T11:46:34Zoai:ri.conicet.gov.ar:11336/14269instacron: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 11:46:34.748CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
title Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
spellingShingle Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
Postigo, Jose Alberto
Dioxygen Initiation
Hydrosilylation
Radical Reactions in Water
Reaction Mechanism
Tri(Trimethylsilyl)Silane
title_short Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
title_full Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
title_fullStr Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
title_full_unstemmed Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
title_sort Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation
dc.creator.none.fl_str_mv Postigo, Jose Alberto
Sbarbati Nudelman, Norma
author Postigo, Jose Alberto
author_facet Postigo, Jose Alberto
Sbarbati Nudelman, Norma
author_role author
author2 Sbarbati Nudelman, Norma
author2_role author
dc.subject.none.fl_str_mv Dioxygen Initiation
Hydrosilylation
Radical Reactions in Water
Reaction Mechanism
Tri(Trimethylsilyl)Silane
topic Dioxygen Initiation
Hydrosilylation
Radical Reactions in Water
Reaction Mechanism
Tri(Trimethylsilyl)Silane
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 relevance of radical initiation metodologies for the classical hydrosilylation reactions of organic compounds bearing C[BOND]C multiple bonds is due to the need to come up with newer and more effcient methods to effect this reaction, on account of its applications on surface chemistry. In the past, when organic solvents were employed, thermal and photochemical methods for the chain initiation reaction have been documented (thermal and photochemical decomposition of azo compounds). We herein present the dioxygen-initiation technique of the classical radical hydrosilylation reaction of C[BOND]C triple bonds with tris(trimethylsilyl)silane ((Me3Si)3SiH) in water. This initiation technique is confronted with the photochemical radical initiation in the absence of a chemical radical precursor other than the silane and also confronted with the classical thermal initiation triggered by the decomposition of an azo compound, both performed in water. The radical-based dioxygen initiation methodology studied in water is shown to afford the highest Z:E stereoselective ratios of hydrosilylated alkenes.
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Belgrano; Argentina
Fil: Sbarbati Nudelman, Norma. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
description The relevance of radical initiation metodologies for the classical hydrosilylation reactions of organic compounds bearing C[BOND]C multiple bonds is due to the need to come up with newer and more effcient methods to effect this reaction, on account of its applications on surface chemistry. In the past, when organic solvents were employed, thermal and photochemical methods for the chain initiation reaction have been documented (thermal and photochemical decomposition of azo compounds). We herein present the dioxygen-initiation technique of the classical radical hydrosilylation reaction of C[BOND]C triple bonds with tris(trimethylsilyl)silane ((Me3Si)3SiH) in water. This initiation technique is confronted with the photochemical radical initiation in the absence of a chemical radical precursor other than the silane and also confronted with the classical thermal initiation triggered by the decomposition of an azo compound, both performed in water. The radical-based dioxygen initiation methodology studied in water is shown to afford the highest Z:E stereoselective ratios of hydrosilylated alkenes.
publishDate 2010
dc.date.none.fl_str_mv 2010-10
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/11336/14269
Postigo, Jose Alberto; Sbarbati Nudelman, Norma; Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation; Wiley; Journal Of Physical Organic Chemistry; 23; 10; 10-2010; 910-914
0894-3230
1099-1395
url http://hdl.handle.net/11336/14269
identifier_str_mv Postigo, Jose Alberto; Sbarbati Nudelman, Norma; Different radical initiation techniques of hydrosilylation reactions of multiple bonds in water: dioxygen initiation; Wiley; Journal Of Physical Organic Chemistry; 23; 10; 10-2010; 910-914
0894-3230
1099-1395
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/poc.1703/abstract
info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.1703
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 Wiley
publisher.none.fl_str_mv Wiley
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 13.10058

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