Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow

We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high‐throughput continuous flow process was developed to perform a dual iridium‐ and nickel‐catalyzed C(sp(2))–C(sp(3)) coupling by circumventing solubility issues associated with po...

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Detalles Bibliográficos
Autores principales: Lima, Fabio, Kabeshov, Mikhail A., Tran, Duc N., Battilocchio, Claudio, Sedelmeier, Joerg, Sedelmeier, Gottfried, Schenkel, Berthold, Ley, Steven V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113707/
https://www.ncbi.nlm.nih.gov/pubmed/27709749
http://dx.doi.org/10.1002/anie.201605548
Descripción
Sumario:We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high‐throughput continuous flow process was developed to perform a dual iridium‐ and nickel‐catalyzed C(sp(2))–C(sp(3)) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine‐derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp(2))–C(sp(3)) coupling method using boronic esters and cyano heteroarenes under flow conditions.

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