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Organocatalyzed, Photoredox Heteroarylation of 2-Trifluoroboratochromanones via C–H Functionalization

[Image: see text] Heteroarylation via C–H functionalization has been synthetically challenging, but such transformations represent an atom-economical and highly convergent route toward complex molecules. Reported herein is a photoredox-catalyzed coupling between 2-trifluoroborato-4-chromanones and v...

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Detalles Bibliográficos
Autores principales: Matsui, Jennifer K., Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5321137/
https://www.ncbi.nlm.nih.gov/pubmed/28157320
http://dx.doi.org/10.1021/acs.orglett.7b00196
Descripción
Sumario:[Image: see text] Heteroarylation via C–H functionalization has been synthetically challenging, but such transformations represent an atom-economical and highly convergent route toward complex molecules. Reported herein is a photoredox-catalyzed coupling between 2-trifluoroborato-4-chromanones and various heteroarenes through a Minisci pathway. Mesitylacridinium perchlorate, an organic photocatalyst, proved to be a better photocatalyst than transition-metal counterparts for such transformations. To highlight the utility of this approach, a library of unprecedented heteroaryl-substituted chromanones was generated that was composed of numerous, specifically substituted molecules containing a broad range of functional groups.