Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones

The coupling between iodobenzene and the enolate anion of acetophenone is accelerated by microwave irradiation. This increase in reaction rate is only ascribed to thermal effects. The coupling reaction gave the corresponding substitution product 1,2-di-phenylethanone in a 50% yield when microwave ir...

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Autores: Caminos, Daniel Alberto, Garro, Alexis, Soria Castro, Silvia Mercedes, Peñeñory, Alicia Beatriz
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/47373
Acceso en línea:http://hdl.handle.net/11336/47373
Access Level:acceso abierto
Palabra clave:Electron-Transfer
Microwave
Radicals
Arylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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repository_id_str
spelling Microwave role in the thermally induced SRN1 reaction for a-arylation of ketonesCaminos, Daniel AlbertoGarro, AlexisSoria Castro, Silvia MercedesPeñeñory, Alicia BeatrizElectron-TransferMicrowaveRadicalsArylationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The coupling between iodobenzene and the enolate anion of acetophenone is accelerated by microwave irradiation. This increase in reaction rate is only ascribed to thermal effects. The coupling reaction gave the corresponding substitution product 1,2-di-phenylethanone in a 50% yield when microwave irradiation was applied between 15–60 s according to the intensity of the pulse. Moreover, this reaction is effective in a temperature window of 70–120 °C. The presence of ionic and dipolar species is not involved in the initiation process as molecular radiators. The excess of tBuOK in the reaction medium may also act as an electron donor helping to generate radicals when the solution temperature increases to 70 °C.Fil: Caminos, Daniel 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: Garro, Alexis. 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: Soria Castro, Silvia Mercedes. 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; ArgentinaThe Royal Society of Chemistry2015-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/47373Caminos, Daniel Alberto; Garro, Alexis; Soria Castro, Silvia Mercedes; Peñeñory, Alicia Beatriz; Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones; The Royal Society of Chemistry; RSC Advances; 5; 2-2015; 20058-200652046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C4RA17055E#info:eu-repo/semantics/altIdentifier/doi/10.1039/c4ra17055einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:33:02Zoai:ri.conicet.gov.ar:11336/47373instacron: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:34982024-05-08 13:33:02.262CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
title Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
spellingShingle Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
Caminos, Daniel Alberto
Electron-Transfer
Microwave
Radicals
Arylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
title_full Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
title_fullStr Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
title_full_unstemmed Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
title_sort Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones
dc.creator.none.fl_str_mv Caminos, Daniel Alberto
Garro, Alexis
Soria Castro, Silvia Mercedes
Peñeñory, Alicia Beatriz
author Caminos, Daniel Alberto
author_facet Caminos, Daniel Alberto
Garro, Alexis
Soria Castro, Silvia Mercedes
Peñeñory, Alicia Beatriz
author_role author
author2 Garro, Alexis
Soria Castro, Silvia Mercedes
Peñeñory, Alicia Beatriz
author2_role author
author
author
dc.subject.none.fl_str_mv Electron-Transfer
Microwave
Radicals
Arylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Electron-Transfer
Microwave
Radicals
Arylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description The coupling between iodobenzene and the enolate anion of acetophenone is accelerated by microwave irradiation. This increase in reaction rate is only ascribed to thermal effects. The coupling reaction gave the corresponding substitution product 1,2-di-phenylethanone in a 50% yield when microwave irradiation was applied between 15–60 s according to the intensity of the pulse. Moreover, this reaction is effective in a temperature window of 70–120 °C. The presence of ionic and dipolar species is not involved in the initiation process as molecular radiators. The excess of tBuOK in the reaction medium may also act as an electron donor helping to generate radicals when the solution temperature increases to 70 °C.
publishDate 2015
dc.date.none.fl_str_mv 2015-02
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/11336/47373
Caminos, Daniel Alberto; Garro, Alexis; Soria Castro, Silvia Mercedes; Peñeñory, Alicia Beatriz; Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones; The Royal Society of Chemistry; RSC Advances; 5; 2-2015; 20058-20065
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47373
identifier_str_mv Caminos, Daniel Alberto; Garro, Alexis; Soria Castro, Silvia Mercedes; Peñeñory, Alicia Beatriz; Microwave role in the thermally induced SRN1 reaction for a-arylation of ketones; The Royal Society of Chemistry; RSC Advances; 5; 2-2015; 20058-20065
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/C4RA17055E#
info:eu-repo/semantics/altIdentifier/doi/10.1039/c4ra17055e
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
application/pdf
dc.publisher.none.fl_str_mv The Royal Society of Chemistry
publisher.none.fl_str_mv The Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,812429

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