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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Detalles Bibliográficos
Autores: Cabrera Afonso, María Jesús, Jaafar, Aida, Cristóbal, Christian, Adrio Sevilla, Francisco Javier, Ribagorda Lobera, María
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/718783
Acceso en línea:http://hdl.handle.net/10486/718783
https://dx.doi.org/10.1021/acs.orglett.5c00082
Access Level:acceso abierto
Palabra clave:Alcohols
alkyls
hydrocarbons
irradiation
reagents
Química
Descripción
Sumario: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