Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
- Autores
- Gaviglio, Carina del Valle; Doctorovich, Fabio
- Año de publicación
- 2008
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Herein we report a study involving the homogeneous catalytic reduction ofunsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media.
Fil: Gaviglio, Carina del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Doctorovich, Fabio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina - Materia
-
Hydrogenation
Catalytic Reduction
Olefins - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/75372
Ver los metadatos del registro completo
id |
CONICETDig_9d644acec05527d3d87b91d781f93d4d |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/75372 |
network_acronym_str |
CONICETDig |
repository_id_str |
3498 |
network_name_str |
CONICET Digital (CONICET) |
spelling |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutionsGaviglio, Carina del ValleDoctorovich, FabioHydrogenationCatalytic ReductionOlefinshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Herein we report a study involving the homogeneous catalytic reduction ofunsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media.Fil: Gaviglio, Carina del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFil: Doctorovich, Fabio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaAmerican Chemical Society2008-07info: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/11336/75372Gaviglio, Carina del Valle; Doctorovich, Fabio; Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions; American Chemical Society; Journal of Organic Chemistry; 73; 14; 7-2008; 5379-53840022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jo800302vinfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo800302vinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:50:49Zoai:ri.conicet.gov.ar:11336/75372instacron: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 09:50:49.832CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
title |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
spellingShingle |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions Gaviglio, Carina del Valle Hydrogenation Catalytic Reduction Olefins |
title_short |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
title_full |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
title_fullStr |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
title_full_unstemmed |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
title_sort |
Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions |
dc.creator.none.fl_str_mv |
Gaviglio, Carina del Valle Doctorovich, Fabio |
author |
Gaviglio, Carina del Valle |
author_facet |
Gaviglio, Carina del Valle Doctorovich, Fabio |
author_role |
author |
author2 |
Doctorovich, Fabio |
author2_role |
author |
dc.subject.none.fl_str_mv |
Hydrogenation Catalytic Reduction Olefins |
topic |
Hydrogenation Catalytic Reduction Olefins |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Herein we report a study involving the homogeneous catalytic reduction ofunsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media. Fil: Gaviglio, Carina del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina Fil: Doctorovich, Fabio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina |
description |
Herein we report a study involving the homogeneous catalytic reduction ofunsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media. |
publishDate |
2008 |
dc.date.none.fl_str_mv |
2008-07 |
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/11336/75372 Gaviglio, Carina del Valle; Doctorovich, Fabio; Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions; American Chemical Society; Journal of Organic Chemistry; 73; 14; 7-2008; 5379-5384 0022-3263 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/75372 |
identifier_str_mv |
Gaviglio, Carina del Valle; Doctorovich, Fabio; Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions; American Chemical Society; Journal of Organic Chemistry; 73; 14; 7-2008; 5379-5384 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/abs/10.1021/jo800302v info:eu-repo/semantics/altIdentifier/doi/10.1021/jo800302v |
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 |
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 |
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_ |
1842269055375900672 |
score |
13.13397 |