Active-iron-promoted hydrodehalogenation of organic halides

Autores
Moglie, Yanina Fernanda; Alonso, Francisco; Vitale, Cristian Alejandro; Yus, Miguel; Radivoy, Gabriel Eduardo
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Under very mild reaction conditions, the active-iron-based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, efficiently performed the hydrodehalogenation of alkyl and aryl halides in tetrahydrofuran at room temperature. The reaction of a series of alkyl and aryl chlorides, bromides, and iodides with this reducing combination led to the formation of the corresponding products resulting from a halogen/hydrogen exchange. Interestingly, the reducing system was efficient in the hydrodehalogenation of aryl fluorides and polychlorinated aromatics. The use of deuterium oxide instead of water in the iron salt allowed the preparation of the corresponding deuterated products. A reaction mechanism has been proposed on the basis of different experiments.
Fil: Moglie, Yanina Fernanda. 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; Argentina
Fil: Alonso, Francisco. Universidad de Alicante; España
Fil: Vitale, Cristian Alejandro. 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; Argentina
Fil: Yus, Miguel. Universidad de Alicante; España
Fil: Radivoy, Gabriel Eduardo. 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; Argentina
Materia
ACTIVE-IRON
HYDRODEHALOGENATION
ORGANIC HALIDES
POLYCHLORINATED AROMATICS
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:11336/94251
Acceder
id CONICETDig_697054678e6e02b972c3ae46c38195a9
oai_identifier_str oai:ri.conicet.gov.ar:11336/94251
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Active-iron-promoted hydrodehalogenation of organic halidesMoglie, Yanina FernandaAlonso, FranciscoVitale, Cristian AlejandroYus, MiguelRadivoy, Gabriel EduardoACTIVE-IRONHYDRODEHALOGENATIONORGANIC HALIDESPOLYCHLORINATED AROMATICShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Under very mild reaction conditions, the active-iron-based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, efficiently performed the hydrodehalogenation of alkyl and aryl halides in tetrahydrofuran at room temperature. The reaction of a series of alkyl and aryl chlorides, bromides, and iodides with this reducing combination led to the formation of the corresponding products resulting from a halogen/hydrogen exchange. Interestingly, the reducing system was efficient in the hydrodehalogenation of aryl fluorides and polychlorinated aromatics. The use of deuterium oxide instead of water in the iron salt allowed the preparation of the corresponding deuterated products. A reaction mechanism has been proposed on the basis of different experiments.Fil: Moglie, Yanina Fernanda. 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: Alonso, Francisco. Universidad de Alicante; EspañaFil: Vitale, Cristian Alejandro. 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: Yus, Miguel. Universidad de Alicante; EspañaFil: Radivoy, Gabriel Eduardo. 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; ArgentinaElsevier Science2006-09-25info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/94251Moglie, Yanina Fernanda; Alonso, Francisco; Vitale, Cristian Alejandro; Yus, Miguel; Radivoy, Gabriel Eduardo; Active-iron-promoted hydrodehalogenation of organic halides; Elsevier Science; Applied Catalysis A: General; 313; 1-2; 25-9-2006; 94-1000926-860XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0926860X06005552info:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2006.07.013info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:40:17Zoai:ri.conicet.gov.ar:11336/94251instacron: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 11:40:18.229CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Active-iron-promoted hydrodehalogenation of organic halides
title Active-iron-promoted hydrodehalogenation of organic halides
spellingShingle Active-iron-promoted hydrodehalogenation of organic halides
Moglie, Yanina Fernanda
ACTIVE-IRON
HYDRODEHALOGENATION
ORGANIC HALIDES
POLYCHLORINATED AROMATICS
title_short Active-iron-promoted hydrodehalogenation of organic halides
title_full Active-iron-promoted hydrodehalogenation of organic halides
title_fullStr Active-iron-promoted hydrodehalogenation of organic halides
title_full_unstemmed Active-iron-promoted hydrodehalogenation of organic halides
title_sort Active-iron-promoted hydrodehalogenation of organic halides
dc.creator.none.fl_str_mv Moglie, Yanina Fernanda
Alonso, Francisco
Vitale, Cristian Alejandro
Yus, Miguel
Radivoy, Gabriel Eduardo
author Moglie, Yanina Fernanda
author_facet Moglie, Yanina Fernanda
Alonso, Francisco
Vitale, Cristian Alejandro
Yus, Miguel
Radivoy, Gabriel Eduardo
author_role author
author2 Alonso, Francisco
Vitale, Cristian Alejandro
Yus, Miguel
Radivoy, Gabriel Eduardo
author2_role author
author
author
author
dc.subject.none.fl_str_mv ACTIVE-IRON
HYDRODEHALOGENATION
ORGANIC HALIDES
POLYCHLORINATED AROMATICS
topic ACTIVE-IRON
HYDRODEHALOGENATION
ORGANIC HALIDES
POLYCHLORINATED AROMATICS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Under very mild reaction conditions, the active-iron-based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, efficiently performed the hydrodehalogenation of alkyl and aryl halides in tetrahydrofuran at room temperature. The reaction of a series of alkyl and aryl chlorides, bromides, and iodides with this reducing combination led to the formation of the corresponding products resulting from a halogen/hydrogen exchange. Interestingly, the reducing system was efficient in the hydrodehalogenation of aryl fluorides and polychlorinated aromatics. The use of deuterium oxide instead of water in the iron salt allowed the preparation of the corresponding deuterated products. A reaction mechanism has been proposed on the basis of different experiments.
Fil: Moglie, Yanina Fernanda. 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; Argentina
Fil: Alonso, Francisco. Universidad de Alicante; España
Fil: Vitale, Cristian Alejandro. 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; Argentina
Fil: Yus, Miguel. Universidad de Alicante; España
Fil: Radivoy, Gabriel Eduardo. 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; Argentina
description Under very mild reaction conditions, the active-iron-based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, efficiently performed the hydrodehalogenation of alkyl and aryl halides in tetrahydrofuran at room temperature. The reaction of a series of alkyl and aryl chlorides, bromides, and iodides with this reducing combination led to the formation of the corresponding products resulting from a halogen/hydrogen exchange. Interestingly, the reducing system was efficient in the hydrodehalogenation of aryl fluorides and polychlorinated aromatics. The use of deuterium oxide instead of water in the iron salt allowed the preparation of the corresponding deuterated products. A reaction mechanism has been proposed on the basis of different experiments.
publishDate 2006
dc.date.none.fl_str_mv 2006-09-25
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/11336/94251
Moglie, Yanina Fernanda; Alonso, Francisco; Vitale, Cristian Alejandro; Yus, Miguel; Radivoy, Gabriel Eduardo; Active-iron-promoted hydrodehalogenation of organic halides; Elsevier Science; Applied Catalysis A: General; 313; 1-2; 25-9-2006; 94-100
0926-860X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/94251
identifier_str_mv Moglie, Yanina Fernanda; Alonso, Francisco; Vitale, Cristian Alejandro; Yus, Miguel; Radivoy, Gabriel Eduardo; Active-iron-promoted hydrodehalogenation of organic halides; Elsevier Science; Applied Catalysis A: General; 313; 1-2; 25-9-2006; 94-100
0926-860X
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/abs/pii/S0926860X06005552
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2006.07.013
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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_ 1846782073370574848
score 12.982451

Publicaciones similares