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.
Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy / Alfano, A. I.; Smyth, M.; Wharry, S.; Moody, T. S.; Baumann, M.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 26:14(2024), pp. 2847-2851. [10.1021/acs.orglett.3c03833]
Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy
Alfano A. I.;
2024
Abstract
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.| File | Dimensione | Formato | |
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