A visible light promoted C–N-coupling of a functionalized pyridazinone with veratrole was developed to forge the central C–N bond of an agrochemical intermediate. Dosing aqueous NaOCl and 4% O₂ in N₂ under blue light irradiation (460 nm) was key to promote the desired transformation while generating benign wastes. Mechanistic studies suggest the formation of a N-chloro species that undergoes selective coupling via a radical pathway induced by the combination of light and oxygen. Further development led to an optimized semi-batch process, which was successfully scaled up to an initial 20 L and then 1.2 m³.

中文翻译：

---

新型光化学 C-N 氧化偶联的开发和放大

开发了一种可见光促进功能化哒嗪酮与藜芦的 C-N 偶联，以形成农业化学中间体的中心 C-N 键。在蓝光照射 (460 nm) 下，在 N ₂中加入 NaOCl 水溶液和 4% O ₂是促进所需转化同时产生良性废物的关键。机理研究表明，通过光和氧的结合诱导的自由基途径进行选择性偶联的 N-氯物种的形成。进一步的开发导致了优化的半间歇工艺，该工艺成功地扩大到最初的 20 L，然后是 1.2 m ³。