Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation

Autores
Lo Fiego, Marcos Jacinto; Badajoz, Mercedes Adriana; Domini, Claudia Elizabeth; Chopa, Alicia Beatriz; Lockhart, María Teresa
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42–84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3–32 h to 10–70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
Fil: Lo Fiego, Marcos Jacinto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Badajoz, Mercedes Adriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Quimica; Argentina
Fil: Domini, Claudia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Quimica; Argentina
Fil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Lockhart, María Teresa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina
Materia
Ultrasound
Solvent-Free
Aromatic Ketones
Arylstannanes
Indium
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/2112
Acceder
id CONICETDig_259502ab2bf9edc9751ea3e8ced6ec3b
oai_identifier_str oai:ri.conicet.gov.ar:11336/2112
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiationLo Fiego, Marcos JacintoBadajoz, Mercedes AdrianaDomini, Claudia ElizabethChopa, Alicia BeatrizLockhart, María TeresaUltrasoundSolvent-FreeAromatic KetonesArylstannanesIndiumhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42–84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3–32 h to 10–70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.Fil: Lo Fiego, Marcos Jacinto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Badajoz, Mercedes Adriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Quimica; ArgentinaFil: Domini, Claudia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Quimica; ArgentinaFil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; ArgentinaFil: Lockhart, María Teresa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; ArgentinaElsevier2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2112Lo Fiego, Marcos Jacinto; Badajoz, Mercedes Adriana; Domini, Claudia Elizabeth; Chopa, Alicia Beatriz; Lockhart, María Teresa; Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation; Elsevier; Ultrasonics Sonochemistry; 20; 3; 5-2013; 826-8321350-4177enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1350417712002441info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ultsonch.2012.10.018info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:02:05Zoai:ri.conicet.gov.ar:11336/2112instacron: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 10:02:05.927CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
title Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
spellingShingle Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
Lo Fiego, Marcos Jacinto
Ultrasound
Solvent-Free
Aromatic Ketones
Arylstannanes
Indium
title_short Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
title_full Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
title_fullStr Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
title_full_unstemmed Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
title_sort Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
dc.creator.none.fl_str_mv Lo Fiego, Marcos Jacinto
Badajoz, Mercedes Adriana
Domini, Claudia Elizabeth
Chopa, Alicia Beatriz
Lockhart, María Teresa
author Lo Fiego, Marcos Jacinto
author_facet Lo Fiego, Marcos Jacinto
Badajoz, Mercedes Adriana
Domini, Claudia Elizabeth
Chopa, Alicia Beatriz
Lockhart, María Teresa
author_role author
author2 Badajoz, Mercedes Adriana
Domini, Claudia Elizabeth
Chopa, Alicia Beatriz
Lockhart, María Teresa
author2_role author
author
author
author
dc.subject.none.fl_str_mv Ultrasound
Solvent-Free
Aromatic Ketones
Arylstannanes
Indium
topic Ultrasound
Solvent-Free
Aromatic Ketones
Arylstannanes
Indium
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 solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42–84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3–32 h to 10–70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
Fil: Lo Fiego, Marcos Jacinto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Badajoz, Mercedes Adriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Quimica; Argentina
Fil: Domini, Claudia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Quimica; Argentina
Fil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Lockhart, María Teresa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - Bahía Blanca. Instituto de Química del Sur; Argentina
description The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42–84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3–32 h to 10–70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
publishDate 2013
dc.date.none.fl_str_mv 2013-05
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/11336/2112
Lo Fiego, Marcos Jacinto; Badajoz, Mercedes Adriana; Domini, Claudia Elizabeth; Chopa, Alicia Beatriz; Lockhart, María Teresa; Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation; Elsevier; Ultrasonics Sonochemistry; 20; 3; 5-2013; 826-832
1350-4177
url http://hdl.handle.net/11336/2112
identifier_str_mv Lo Fiego, Marcos Jacinto; Badajoz, Mercedes Adriana; Domini, Claudia Elizabeth; Chopa, Alicia Beatriz; Lockhart, María Teresa; Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation; Elsevier; Ultrasonics Sonochemistry; 20; 3; 5-2013; 826-832
1350-4177
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1350417712002441
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ultsonch.2012.10.018
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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_ 1842269736958689280
score 13.13397

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