Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design

Autores
Luong, Martin; Domini, Claudia Elizabeth; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.
Fil: Luong, Martin. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Domini, Claudia Elizabeth. Universidad Nacional del Sur. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Materia
Ultrasound
Stille Cross-Coupling
Aromatic Ketones
Arylstannanes
Experimental Design
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:11336/2114
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental designLuong, MartinDomini, Claudia ElizabethSilbestri, Gustavo FabiánChopa, Alicia BeatrizUltrasoundStille Cross-CouplingAromatic KetonesArylstannanesExperimental Designhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.Fil: Luong, Martin. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; ArgentinaFil: Domini, Claudia Elizabeth. Universidad Nacional del Sur. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; ArgentinaFil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; ArgentinaFil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; ArgentinaElsevier2013-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2114Luong, Martin; Domini, Claudia Elizabeth; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design; Elsevier; Journal of Organometallic Chemistry; 723; 1-1-2013; 43-480022-328Xenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2012.10.026info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022328X12006158info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:00:48Zoai:ri.conicet.gov.ar:11336/2114instacron: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 10:00:48.439CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
title Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
spellingShingle Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
Luong, Martin
Ultrasound
Stille Cross-Coupling
Aromatic Ketones
Arylstannanes
Experimental Design
title_short Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
title_full Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
title_fullStr Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
title_full_unstemmed Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
title_sort Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
dc.creator.none.fl_str_mv Luong, Martin
Domini, Claudia Elizabeth
Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
author Luong, Martin
author_facet Luong, Martin
Domini, Claudia Elizabeth
Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
author_role author
author2 Domini, Claudia Elizabeth
Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
author2_role author
author
author
dc.subject.none.fl_str_mv Ultrasound
Stille Cross-Coupling
Aromatic Ketones
Arylstannanes
Experimental Design
topic Ultrasound
Stille Cross-Coupling
Aromatic Ketones
Arylstannanes
Experimental Design
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.
Fil: Luong, Martin. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Domini, Claudia Elizabeth. Universidad Nacional del Sur. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
Fil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
description A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.
publishDate 2013
dc.date.none.fl_str_mv 2013-01-01
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/11336/2114
Luong, Martin; Domini, Claudia Elizabeth; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design; Elsevier; Journal of Organometallic Chemistry; 723; 1-1-2013; 43-48
0022-328X
url http://hdl.handle.net/11336/2114
identifier_str_mv Luong, Martin; Domini, Claudia Elizabeth; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design; Elsevier; Journal of Organometallic Chemistry; 723; 1-1-2013; 43-48
0022-328X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2012.10.026
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022328X12006158
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
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score 13.13397

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