Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds

Autores
Moglie, Yanina Fernanda; Vitale, Cristian Alejandro; Radivoy, Gabriel Eduardo
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount of 4,4´-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.
Fil: Moglie, Yanina Fernanda. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Fil: Vitale, Cristian Alejandro. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Fil: Radivoy, Gabriel Eduardo. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Materia
ACTIVE IRON
REDUCTIVE COUPLING
NITRO COMPOUNDS
AZOCOMPOUNDS
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:11336/240772
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compoundsMoglie, Yanina FernandaVitale, Cristian AlejandroRadivoy, Gabriel EduardoACTIVE IRONREDUCTIVE COUPLINGNITRO COMPOUNDSAZOCOMPOUNDShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount of 4,4´-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.Fil: Moglie, Yanina Fernanda. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; ArgentinaFil: Vitale, Cristian Alejandro. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; ArgentinaFil: Radivoy, Gabriel Eduardo. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; ArgentinaPergamon-Elsevier Science Ltd2008-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/240772Moglie, Yanina Fernanda; Vitale, Cristian Alejandro; Radivoy, Gabriel Eduardo; Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 49; 11; 8-2008; 1828-18310040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040403908000920info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2008.01.053info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:09:12Zoai:ri.conicet.gov.ar:11336/240772instacron: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:34982025-10-22 12:09:13.043CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
title Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
spellingShingle Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
Moglie, Yanina Fernanda
ACTIVE IRON
REDUCTIVE COUPLING
NITRO COMPOUNDS
AZOCOMPOUNDS
title_short Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
title_full Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
title_fullStr Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
title_full_unstemmed Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
title_sort Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
dc.creator.none.fl_str_mv Moglie, Yanina Fernanda
Vitale, Cristian Alejandro
Radivoy, Gabriel Eduardo
author Moglie, Yanina Fernanda
author_facet Moglie, Yanina Fernanda
Vitale, Cristian Alejandro
Radivoy, Gabriel Eduardo
author_role author
author2 Vitale, Cristian Alejandro
Radivoy, Gabriel Eduardo
author2_role author
author
dc.subject.none.fl_str_mv ACTIVE IRON
REDUCTIVE COUPLING
NITRO COMPOUNDS
AZOCOMPOUNDS
topic ACTIVE IRON
REDUCTIVE COUPLING
NITRO COMPOUNDS
AZOCOMPOUNDS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount of 4,4´-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.
Fil: Moglie, Yanina Fernanda. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Fil: Vitale, Cristian Alejandro. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Fil: Radivoy, Gabriel Eduardo. Universidad Nacional del Sur; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
description Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount of 4,4´-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.
publishDate 2008
dc.date.none.fl_str_mv 2008-08
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/11336/240772
Moglie, Yanina Fernanda; Vitale, Cristian Alejandro; Radivoy, Gabriel Eduardo; Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 49; 11; 8-2008; 1828-1831
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240772
identifier_str_mv Moglie, Yanina Fernanda; Vitale, Cristian Alejandro; Radivoy, Gabriel Eduardo; Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 49; 11; 8-2008; 1828-1831
0040-4039
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://www.sciencedirect.com/science/article/pii/S0040403908000920
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2008.01.053
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 12.982451

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