Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes

Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free pr...

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Autores: Lo Fiego, Marcos Jacinto, Silbestri, Gustavo Fabián, Chopa, Alicia Beatriz, Lockhart, María Teresa
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2011
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/99639
Acesso em linha:http://hdl.handle.net/11336/99639
Access Level:acceso abierto
Palavra-chave:STERICALLY DIARYL KETONES
ARYLSTANNANES
ALCL3
INDIUM
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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oai_identifier_str oai:ri.conicet.gov.ar:11336/99639
network_acronym_str AR
network_name_str Argentina
repository_id_str
spelling Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanesLo Fiego, Marcos JacintoSilbestri, Gustavo FabiánChopa, Alicia BeatrizLockhart, María TeresaSTERICALLY DIARYL KETONESARYLSTANNANESALCL3INDIUMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl 3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.Fil: Lo Fiego, Marcos Jacinto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Chopa, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. 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. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaAmerican Chemical Society2011-03info: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/11336/99639Lo Fiego, Marcos Jacinto; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Lockhart, María Teresa; Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes; American Chemical Society; Journal of Organic Chemistry; 76; 6; 3-2011; 1707-17140022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo102366qinfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo102366qinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:50:15Zoai:ri.conicet.gov.ar:11336/99639instacron: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 13:50:15.818CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
title Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
spellingShingle Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
Lo Fiego, Marcos Jacinto
STERICALLY DIARYL KETONES
ARYLSTANNANES
ALCL3
INDIUM
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
title_full Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
title_fullStr Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
title_full_unstemmed Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
title_sort Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
dc.creator.none.fl_str_mv Lo Fiego, Marcos Jacinto
Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
Lockhart, María Teresa
author Lo Fiego, Marcos Jacinto
author_facet Lo Fiego, Marcos Jacinto
Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
Lockhart, María Teresa
author_role author
author2 Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
Lockhart, María Teresa
author2_role author
author
author
dc.subject.none.fl_str_mv STERICALLY DIARYL KETONES
ARYLSTANNANES
ALCL3
INDIUM
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic STERICALLY DIARYL KETONES
ARYLSTANNANES
ALCL3
INDIUM
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl 3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.
publishDate 2011
dc.date.none.fl_str_mv 2011-03
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/11336/99639
Lo Fiego, Marcos Jacinto; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Lockhart, María Teresa; Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes; American Chemical Society; Journal of Organic Chemistry; 76; 6; 3-2011; 1707-1714
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/99639
identifier_str_mv Lo Fiego, Marcos Jacinto; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Lockhart, María Teresa; Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes; American Chemical Society; Journal of Organic Chemistry; 76; 6; 3-2011; 1707-1714
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo102366q
info:eu-repo/semantics/altIdentifier/doi/10.1021/jo102366q
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
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 15,811543

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