Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold

Autores
Del Castillo, Estefanía; Martinez, Mario David; Bosnidou, Alexandra E.; Duhamel, Thomas; O'Broin, Calvin Q.; Zhang, Hongwei; Escudero Adán, Eduardo C.; Martínez Belmonte, Marta; Muñiz, Kilian
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.
Fil: Del Castillo, Estefanía. Institute of Chemical Research of Catalonia; España
Fil: Martinez, Mario David. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Bosnidou, Alexandra E.. Institute of Chemical Research of Catalonia; España
Fil: Duhamel, Thomas. Universidad de Oviedo; España
Fil: O'Broin, Calvin Q.. Institute of Chemical Research of Catalonia; España
Fil: Zhang, Hongwei. Institute of Chemical Research of Catalonia; España
Fil: Escudero Adán, Eduardo C.. Institute of Chemical Research of Catalonia; España
Fil: Martínez Belmonte, Marta. Institute of Chemical Research of Catalonia; España
Fil: Muñiz, Kilian. Institute of Chemical Research of Catalonia; España
Materia
BROMINE
C−H FUNCTIONALIZATION
HOFMANN–LÖFFLER REACTION
IODINE
POLYHALOGENATION
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:11336/182443
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/182443
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler ManifoldDel Castillo, EstefaníaMartinez, Mario DavidBosnidou, Alexandra E.Duhamel, ThomasO'Broin, Calvin Q.Zhang, HongweiEscudero Adán, Eduardo C.Martínez Belmonte, MartaMuñiz, KilianBROMINEC−H FUNCTIONALIZATIONHOFMANN–LÖFFLER REACTIONIODINEPOLYHALOGENATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.Fil: Del Castillo, Estefanía. Institute of Chemical Research of Catalonia; EspañaFil: Martinez, Mario David. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Bosnidou, Alexandra E.. Institute of Chemical Research of Catalonia; EspañaFil: Duhamel, Thomas. Universidad de Oviedo; EspañaFil: O'Broin, Calvin Q.. Institute of Chemical Research of Catalonia; EspañaFil: Zhang, Hongwei. Institute of Chemical Research of Catalonia; EspañaFil: Escudero Adán, Eduardo C.. Institute of Chemical Research of Catalonia; EspañaFil: Martínez Belmonte, Marta. Institute of Chemical Research of Catalonia; EspañaFil: Muñiz, Kilian. Institute of Chemical Research of Catalonia; EspañaWiley VCH Verlag2018-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/182443Del Castillo, Estefanía; Martinez, Mario David; Bosnidou, Alexandra E.; Duhamel, Thomas; O'Broin, Calvin Q.; et al.; Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold; Wiley VCH Verlag; Chemistry- A European Journal; 24; 65; 9-2018; 17225-172290947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201804504info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201804504info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:44Zoai:ri.conicet.gov.ar:11336/182443instacron: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:34982025-09-29 09:39:45.094CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
title Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
spellingShingle Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
Del Castillo, Estefanía
BROMINE
C−H FUNCTIONALIZATION
HOFMANN–LÖFFLER REACTION
IODINE
POLYHALOGENATION
title_short Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
title_full Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
title_fullStr Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
title_full_unstemmed Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
title_sort Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
dc.creator.none.fl_str_mv Del Castillo, Estefanía
Martinez, Mario David
Bosnidou, Alexandra E.
Duhamel, Thomas
O'Broin, Calvin Q.
Zhang, Hongwei
Escudero Adán, Eduardo C.
Martínez Belmonte, Marta
Muñiz, Kilian
author Del Castillo, Estefanía
author_facet Del Castillo, Estefanía
Martinez, Mario David
Bosnidou, Alexandra E.
Duhamel, Thomas
O'Broin, Calvin Q.
Zhang, Hongwei
Escudero Adán, Eduardo C.
Martínez Belmonte, Marta
Muñiz, Kilian
author_role author
author2 Martinez, Mario David
Bosnidou, Alexandra E.
Duhamel, Thomas
O'Broin, Calvin Q.
Zhang, Hongwei
Escudero Adán, Eduardo C.
Martínez Belmonte, Marta
Muñiz, Kilian
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv BROMINE
C−H FUNCTIONALIZATION
HOFMANN–LÖFFLER REACTION
IODINE
POLYHALOGENATION
topic BROMINE
C−H FUNCTIONALIZATION
HOFMANN–LÖFFLER REACTION
IODINE
POLYHALOGENATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.
Fil: Del Castillo, Estefanía. Institute of Chemical Research of Catalonia; España
Fil: Martinez, Mario David. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Bosnidou, Alexandra E.. Institute of Chemical Research of Catalonia; España
Fil: Duhamel, Thomas. Universidad de Oviedo; España
Fil: O'Broin, Calvin Q.. Institute of Chemical Research of Catalonia; España
Fil: Zhang, Hongwei. Institute of Chemical Research of Catalonia; España
Fil: Escudero Adán, Eduardo C.. Institute of Chemical Research of Catalonia; España
Fil: Martínez Belmonte, Marta. Institute of Chemical Research of Catalonia; España
Fil: Muñiz, Kilian. Institute of Chemical Research of Catalonia; España
description An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.
publishDate 2018
dc.date.none.fl_str_mv 2018-09
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/11336/182443
Del Castillo, Estefanía; Martinez, Mario David; Bosnidou, Alexandra E.; Duhamel, Thomas; O'Broin, Calvin Q.; et al.; Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold; Wiley VCH Verlag; Chemistry- A European Journal; 24; 65; 9-2018; 17225-17229
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/182443
identifier_str_mv Del Castillo, Estefanía; Martinez, Mario David; Bosnidou, Alexandra E.; Duhamel, Thomas; O'Broin, Calvin Q.; et al.; Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold; Wiley VCH Verlag; Chemistry- A European Journal; 24; 65; 9-2018; 17225-17229
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/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201804504
info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201804504
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
_version_ 1844613258136256512
score 13.070432

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