Organic synthesis in water mediated by silyl radicals

Autores
Barata Vallejo, Sebastian; Sbarbati, Norma Ethel; Postigo, Jose Alberto
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This account is focused on highlighting the recent advances on synthetically-useful organic reactions employing siliconcentered radicals in water, and presenting new reactions in water, mediated by silyl radicals. In doing so, several types of organic radical transformations will be discussed, such as reduction of organic halides utilizing non toxic organosilane reducing agents in water, transformation of azides into amines, synthesis of protecting silyl ethers in water, hydrosilylation reactions of carbon-carbon double and triple bonds, and radical cyclization reactions in water induced by silicon-centered radicals. More recently, intermolecular radical carboncarbon bond formation reactions mediated by silyl radicals have allowed the synthesis of perfluoroalkyl-substituted compounds in water, widening the scope for the syntheses of fluorophoes. These silicon radical-mediated chain reactions in water are initiated through different methods, among which, thermal, photochemical, and dioxygen initiations are reported to be the most successful methods in water. A versatile aspect of the radical methodology employed in water will be presented in terms of dealing with water-soluble and organic solvent- soluble substrates in these silicon radical-mediated reactions in water. In this regard, for an efficient chain process to take place in water, a chain carrier must be used when water-soluble substrates are employed, whereas organic solvent-soluble materials do not require a chain transporter when silyl radicals are used in water.
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Sbarbati, Norma Ethel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Silyl Radicals
Silyl Radicals in Water
Radical Carbon-Carbon Bond Formation in Water
Chain Carrier
Aibn
Triethyl Borane (Et3b)
Dioxygen
Photochemical Radical Initiation
Dihydrochloride (Aaph)
Accn Initiation
(Me3si) 3sih
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:11336/16260
Acceder
id CONICETDig_309444c7b4819c487d8f8dff15030ae8
oai_identifier_str oai:ri.conicet.gov.ar:11336/16260
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Organic synthesis in water mediated by silyl radicalsBarata Vallejo, SebastianSbarbati, Norma EthelPostigo, Jose AlbertoSilyl RadicalsSilyl Radicals in WaterRadical Carbon-Carbon Bond Formation in WaterChain CarrierAibnTriethyl Borane (Et3b)DioxygenPhotochemical Radical InitiationDihydrochloride (Aaph)Accn Initiation(Me3si) 3sihhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This account is focused on highlighting the recent advances on synthetically-useful organic reactions employing siliconcentered radicals in water, and presenting new reactions in water, mediated by silyl radicals. In doing so, several types of organic radical transformations will be discussed, such as reduction of organic halides utilizing non toxic organosilane reducing agents in water, transformation of azides into amines, synthesis of protecting silyl ethers in water, hydrosilylation reactions of carbon-carbon double and triple bonds, and radical cyclization reactions in water induced by silicon-centered radicals. More recently, intermolecular radical carboncarbon bond formation reactions mediated by silyl radicals have allowed the synthesis of perfluoroalkyl-substituted compounds in water, widening the scope for the syntheses of fluorophoes. These silicon radical-mediated chain reactions in water are initiated through different methods, among which, thermal, photochemical, and dioxygen initiations are reported to be the most successful methods in water. A versatile aspect of the radical methodology employed in water will be presented in terms of dealing with water-soluble and organic solvent- soluble substrates in these silicon radical-mediated reactions in water. In this regard, for an efficient chain process to take place in water, a chain carrier must be used when water-soluble substrates are employed, whereas organic solvent-soluble materials do not require a chain transporter when silyl radicals are used in water.Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Sbarbati, Norma Ethel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaBentham Science Publishers2011-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/16260Barata Vallejo, Sebastian; Sbarbati, Norma Ethel; Postigo, Jose Alberto; Organic synthesis in water mediated by silyl radicals; Bentham Science Publishers; Current Organic Chemistry; 15; 11; 6-2011; 1826-18421385-27281875-5348enginfo:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/74029info:eu-repo/semantics/altIdentifier/doi/10.2174/138527211795656589info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-29T12:20:55Zoai:ri.conicet.gov.ar:11336/16260instacron: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 12:20:55.807CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Organic synthesis in water mediated by silyl radicals
title Organic synthesis in water mediated by silyl radicals
spellingShingle Organic synthesis in water mediated by silyl radicals
Barata Vallejo, Sebastian
Silyl Radicals
Silyl Radicals in Water
Radical Carbon-Carbon Bond Formation in Water
Chain Carrier
Aibn
Triethyl Borane (Et3b)
Dioxygen
Photochemical Radical Initiation
Dihydrochloride (Aaph)
Accn Initiation
(Me3si) 3sih
title_short Organic synthesis in water mediated by silyl radicals
title_full Organic synthesis in water mediated by silyl radicals
title_fullStr Organic synthesis in water mediated by silyl radicals
title_full_unstemmed Organic synthesis in water mediated by silyl radicals
title_sort Organic synthesis in water mediated by silyl radicals
dc.creator.none.fl_str_mv Barata Vallejo, Sebastian
Sbarbati, Norma Ethel
Postigo, Jose Alberto
author Barata Vallejo, Sebastian
author_facet Barata Vallejo, Sebastian
Sbarbati, Norma Ethel
Postigo, Jose Alberto
author_role author
author2 Sbarbati, Norma Ethel
Postigo, Jose Alberto
author2_role author
author
dc.subject.none.fl_str_mv Silyl Radicals
Silyl Radicals in Water
Radical Carbon-Carbon Bond Formation in Water
Chain Carrier
Aibn
Triethyl Borane (Et3b)
Dioxygen
Photochemical Radical Initiation
Dihydrochloride (Aaph)
Accn Initiation
(Me3si) 3sih
topic Silyl Radicals
Silyl Radicals in Water
Radical Carbon-Carbon Bond Formation in Water
Chain Carrier
Aibn
Triethyl Borane (Et3b)
Dioxygen
Photochemical Radical Initiation
Dihydrochloride (Aaph)
Accn Initiation
(Me3si) 3sih
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This account is focused on highlighting the recent advances on synthetically-useful organic reactions employing siliconcentered radicals in water, and presenting new reactions in water, mediated by silyl radicals. In doing so, several types of organic radical transformations will be discussed, such as reduction of organic halides utilizing non toxic organosilane reducing agents in water, transformation of azides into amines, synthesis of protecting silyl ethers in water, hydrosilylation reactions of carbon-carbon double and triple bonds, and radical cyclization reactions in water induced by silicon-centered radicals. More recently, intermolecular radical carboncarbon bond formation reactions mediated by silyl radicals have allowed the synthesis of perfluoroalkyl-substituted compounds in water, widening the scope for the syntheses of fluorophoes. These silicon radical-mediated chain reactions in water are initiated through different methods, among which, thermal, photochemical, and dioxygen initiations are reported to be the most successful methods in water. A versatile aspect of the radical methodology employed in water will be presented in terms of dealing with water-soluble and organic solvent- soluble substrates in these silicon radical-mediated reactions in water. In this regard, for an efficient chain process to take place in water, a chain carrier must be used when water-soluble substrates are employed, whereas organic solvent-soluble materials do not require a chain transporter when silyl radicals are used in water.
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Sbarbati, Norma Ethel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description This account is focused on highlighting the recent advances on synthetically-useful organic reactions employing siliconcentered radicals in water, and presenting new reactions in water, mediated by silyl radicals. In doing so, several types of organic radical transformations will be discussed, such as reduction of organic halides utilizing non toxic organosilane reducing agents in water, transformation of azides into amines, synthesis of protecting silyl ethers in water, hydrosilylation reactions of carbon-carbon double and triple bonds, and radical cyclization reactions in water induced by silicon-centered radicals. More recently, intermolecular radical carboncarbon bond formation reactions mediated by silyl radicals have allowed the synthesis of perfluoroalkyl-substituted compounds in water, widening the scope for the syntheses of fluorophoes. These silicon radical-mediated chain reactions in water are initiated through different methods, among which, thermal, photochemical, and dioxygen initiations are reported to be the most successful methods in water. A versatile aspect of the radical methodology employed in water will be presented in terms of dealing with water-soluble and organic solvent- soluble substrates in these silicon radical-mediated reactions in water. In this regard, for an efficient chain process to take place in water, a chain carrier must be used when water-soluble substrates are employed, whereas organic solvent-soluble materials do not require a chain transporter when silyl radicals are used in water.
publishDate 2011
dc.date.none.fl_str_mv 2011-06
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/11336/16260
Barata Vallejo, Sebastian; Sbarbati, Norma Ethel; Postigo, Jose Alberto; Organic synthesis in water mediated by silyl radicals; Bentham Science Publishers; Current Organic Chemistry; 15; 11; 6-2011; 1826-1842
1385-2728
1875-5348
url http://hdl.handle.net/11336/16260
identifier_str_mv Barata Vallejo, Sebastian; Sbarbati, Norma Ethel; Postigo, Jose Alberto; Organic synthesis in water mediated by silyl radicals; Bentham Science Publishers; Current Organic Chemistry; 15; 11; 6-2011; 1826-1842
1385-2728
1875-5348
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/74029
info:eu-repo/semantics/altIdentifier/doi/10.2174/138527211795656589
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
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
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_ 1847427113868591104
score 12.589754

Publicaciones similares