Modular Synthesis of Benzoylpyridines Exploiting a Reductive Arylation Strategy

Org Lett. 2024 Apr 12;26(14):2847-2851. doi: 10.1021/acs.orglett.3c03833. Epub 2023 Dec 22.

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.