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A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation

An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method d...

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Detalles Bibliográficos
Autores principales: Sharique, Mohammed, Majhi, Jadab, Dhungana, Roshan K., Kammer, Lisa Marie, Krumb, Matthias, Lipp, Alexander, Romero, Eugénie, Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9116295/
https://www.ncbi.nlm.nih.gov/pubmed/35694363
http://dx.doi.org/10.1039/d2sc01363k
Descripción
Sumario:An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate.