Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes

We report a metal-free synthesis of highly functionalized 1,6-amino alcohols through a visible-light 1,2-carboimination of alkenes and bifunctional starting materials prepared from commercially available alcohols. This protocol orchestrates the generation of up to four different types of radicals, w...

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Detalhes bibliográficos
Autores: Cabrera Afonso, María Jesús, Jaafar, Aida, Cristóbal, Christian, Adrio Sevilla, Francisco Javier, Ribagorda Lobera, María
Formato: artículo
Fecha de publicación:2025
País:España
Recursos:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/718783
Acesso em linha:http://hdl.handle.net/10486/718783
https://dx.doi.org/10.1021/acs.orglett.5c00082
Access Level:acceso abierto
Palavra-chave:Alcohols
alkyls
hydrocarbons
irradiation
reagents
Química
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spelling Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenesCabrera Afonso, María JesúsJaafar, AidaCristóbal, ChristianAdrio Sevilla, Francisco JavierRibagorda Lobera, MaríaAlcoholsalkylshydrocarbonsirradiationreagentsQuímicaWe report a metal-free synthesis of highly functionalized 1,6-amino alcohols through a visible-light 1,2-carboimination of alkenes and bifunctional starting materials prepared from commercially available alcohols. This protocol orchestrates the generation of up to four different types of radicals, which are efficiently recombined to yield 1,6-iminyl alcohols. The methodology demonstrated a broad functional group tolerance and was validated by the late-stage installation of the 1,6-amino alcohol motif in biomolecules and pharmaceuticals and the scale-up of the process. The versatility of the products was highlighted by their conversion into a variety of useful intermediates for target-directed synthesisThe authors thank Ministerio de Ciencia, Innovación y Universidades-Agencia Estatal de Investigación (Grants PID2023-146801NB-C32, PID2020-113059GB-C22, and PID2021-1248553NB-100), and the European Union’s Horizon 2020 research and innovation programme under Grant Agreement 101034324.American Chemical SocietyDepartamento de Química OrgánicaFacultad de Ciencias20252025-03-03research articlehttp://purl.org/coar/resource_type/c_2df8fbb1AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/718783https://dx.doi.org/10.1021/acs.orglett.5c00082reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7187832026-06-23T12:46:27Z
dc.title.none.fl_str_mv Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
title Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
spellingShingle Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
Cabrera Afonso, María Jesús
Alcohols
alkyls
hydrocarbons
irradiation
reagents
Química
title_short Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
title_full Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
title_fullStr Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
title_full_unstemmed Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
title_sort Visible-light-promoted synthesis of 1,6-imino alcohols by metal-free 1,2-carboimination of alkenes
dc.creator.none.fl_str_mv Cabrera Afonso, María Jesús
Jaafar, Aida
Cristóbal, Christian
Adrio Sevilla, Francisco Javier
Ribagorda Lobera, María
author Cabrera Afonso, María Jesús
author_facet Cabrera Afonso, María Jesús
Jaafar, Aida
Cristóbal, Christian
Adrio Sevilla, Francisco Javier
Ribagorda Lobera, María
author_role author
author2 Jaafar, Aida
Cristóbal, Christian
Adrio Sevilla, Francisco Javier
Ribagorda Lobera, María
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Alcohols
alkyls
hydrocarbons
irradiation
reagents
Química
topic Alcohols
alkyls
hydrocarbons
irradiation
reagents
Química
description We report a metal-free synthesis of highly functionalized 1,6-amino alcohols through a visible-light 1,2-carboimination of alkenes and bifunctional starting materials prepared from commercially available alcohols. This protocol orchestrates the generation of up to four different types of radicals, which are efficiently recombined to yield 1,6-iminyl alcohols. The methodology demonstrated a broad functional group tolerance and was validated by the late-stage installation of the 1,6-amino alcohol motif in biomolecules and pharmaceuticals and the scale-up of the process. The versatility of the products was highlighted by their conversion into a variety of useful intermediates for target-directed synthesis
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-03-03
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/718783
https://dx.doi.org/10.1021/acs.orglett.5c00082
url http://hdl.handle.net/10486/718783
https://dx.doi.org/10.1021/acs.orglett.5c00082
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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