Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent

Autores
Barluenga, José; González Bobes, Francisco; Murguia, Marcelo Cesar; Ananthoju, Sreenivasa; González, José
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The use of bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) as an oxidizing agent towards different types of alcohols is reported. The observed reactivity involves different reaction pathways, as a function both of the structures of the starting materials and of the experimental conditions. Interestingly, the title iodine-containing compound is capable of a tuneable reaction with simple cycloalkanols, providing straight and selective access either to ω-iodocarbonyl compounds or to ketones, a previously unreported and chemoselective range of oxidation potential. Furthermore, appropriate conditions for the preparation of aldehydes and esters from primary alcohols by easily performed experimental procedures were also established. The β-scission reactions of cycloalkanols and the α-oxidation processes of primary, secondary and benzylic alcohols are discussed.
Fil: Barluenga, José. Universidad de Oviedo; España
Fil: González Bobes, Francisco. Universidad de Oviedo; España
Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina. Universidad de Oviedo; España
Fil: Ananthoju, Sreenivasa. Universidad de Oviedo; España
Fil: González, José. Universidad de Oviedo; España
Materia
Oxidations
Iodations
Iodonium
Bis Pyridine Iodonium
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:11336/26833
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagentBarluenga, JoséGonzález Bobes, FranciscoMurguia, Marcelo CesarAnanthoju, SreenivasaGonzález, JoséOxidationsIodationsIodoniumBis Pyridine Iodoniumhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The use of bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) as an oxidizing agent towards different types of alcohols is reported. The observed reactivity involves different reaction pathways, as a function both of the structures of the starting materials and of the experimental conditions. Interestingly, the title iodine-containing compound is capable of a tuneable reaction with simple cycloalkanols, providing straight and selective access either to ω-iodocarbonyl compounds or to ketones, a previously unreported and chemoselective range of oxidation potential. Furthermore, appropriate conditions for the preparation of aldehydes and esters from primary alcohols by easily performed experimental procedures were also established. The β-scission reactions of cycloalkanols and the α-oxidation processes of primary, secondary and benzylic alcohols are discussed.Fil: Barluenga, José. Universidad de Oviedo; EspañaFil: González Bobes, Francisco. Universidad de Oviedo; EspañaFil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina. Universidad de Oviedo; EspañaFil: Ananthoju, Sreenivasa. Universidad de Oviedo; EspañaFil: González, José. Universidad de Oviedo; EspañaWiley VCH Verlag2004-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/26833Barluenga, José; González Bobes, Francisco; Murguia, Marcelo Cesar; Ananthoju, Sreenivasa; González, José; Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent; Wiley VCH Verlag; Chemistry- A European Journal; 10; 17; 7-2004; 4206-42130947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200400136info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.200400136/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:06:47Zoai:ri.conicet.gov.ar:11336/26833instacron: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 10:06:47.611CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
title Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
spellingShingle Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
Barluenga, José
Oxidations
Iodations
Iodonium
Bis Pyridine Iodonium
title_short Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
title_full Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
title_fullStr Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
title_full_unstemmed Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
title_sort Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent
dc.creator.none.fl_str_mv Barluenga, José
González Bobes, Francisco
Murguia, Marcelo Cesar
Ananthoju, Sreenivasa
González, José
author Barluenga, José
author_facet Barluenga, José
González Bobes, Francisco
Murguia, Marcelo Cesar
Ananthoju, Sreenivasa
González, José
author_role author
author2 González Bobes, Francisco
Murguia, Marcelo Cesar
Ananthoju, Sreenivasa
González, José
author2_role author
author
author
author
dc.subject.none.fl_str_mv Oxidations
Iodations
Iodonium
Bis Pyridine Iodonium
topic Oxidations
Iodations
Iodonium
Bis Pyridine Iodonium
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The use of bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) as an oxidizing agent towards different types of alcohols is reported. The observed reactivity involves different reaction pathways, as a function both of the structures of the starting materials and of the experimental conditions. Interestingly, the title iodine-containing compound is capable of a tuneable reaction with simple cycloalkanols, providing straight and selective access either to ω-iodocarbonyl compounds or to ketones, a previously unreported and chemoselective range of oxidation potential. Furthermore, appropriate conditions for the preparation of aldehydes and esters from primary alcohols by easily performed experimental procedures were also established. The β-scission reactions of cycloalkanols and the α-oxidation processes of primary, secondary and benzylic alcohols are discussed.
Fil: Barluenga, José. Universidad de Oviedo; España
Fil: González Bobes, Francisco. Universidad de Oviedo; España
Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina. Universidad de Oviedo; España
Fil: Ananthoju, Sreenivasa. Universidad de Oviedo; España
Fil: González, José. Universidad de Oviedo; España
description The use of bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) as an oxidizing agent towards different types of alcohols is reported. The observed reactivity involves different reaction pathways, as a function both of the structures of the starting materials and of the experimental conditions. Interestingly, the title iodine-containing compound is capable of a tuneable reaction with simple cycloalkanols, providing straight and selective access either to ω-iodocarbonyl compounds or to ketones, a previously unreported and chemoselective range of oxidation potential. Furthermore, appropriate conditions for the preparation of aldehydes and esters from primary alcohols by easily performed experimental procedures were also established. The β-scission reactions of cycloalkanols and the α-oxidation processes of primary, secondary and benzylic alcohols are discussed.
publishDate 2004
dc.date.none.fl_str_mv 2004-07
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/11336/26833
Barluenga, José; González Bobes, Francisco; Murguia, Marcelo Cesar; Ananthoju, Sreenivasa; González, José; Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent; Wiley VCH Verlag; Chemistry- A European Journal; 10; 17; 7-2004; 4206-4213
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/26833
identifier_str_mv Barluenga, José; González Bobes, Francisco; Murguia, Marcelo Cesar; Ananthoju, Sreenivasa; González, José; Bis(pyridine)iodonium Tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent; Wiley VCH Verlag; Chemistry- A European Journal; 10; 17; 7-2004; 4206-4213
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200400136
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.200400136/abstract
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
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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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