Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy

Herein we disclose a telescoped flow strategy to access electronically differentiated bisaryl ketones as potentially new and tunable photosensitizers containing both electron-rich benzene systems and electron-deficient pyridyl moieties. Our approach merges a light-driven (365 nm) and catalyst-free r...

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Veröffentlicht in:Organic letters 2024-04, Vol.26 (14), p.2847-2851
Hauptverfasser: Alfano, Antonella Ilenia, Smyth, Megan, Wharry, Scott, Moody, Thomas S., Baumann, Marcus
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein we disclose a telescoped flow strategy to access electronically differentiated bisaryl ketones as potentially new and tunable photosensitizers containing both electron-rich benzene systems and electron-deficient pyridyl moieties. Our approach merges a light-driven (365 nm) and catalyst-free reductive arylation between aromatic aldehydes and cyanopyridines with a subsequent oxidation process. The addition of electron-donating and withdrawing substituents on the scaffold allowed effective modification of the absorbance of these compounds in the UV–vis region, while the continuous flow process affords high yields, short residence time, and high throughput.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c03833