Photoinduced Deconstructive Alkylation Approach Enabled by Oxy-Radicals from Alcohols

作者：Yiman Gao, Yan Li, W. B. Yan, Kui Zhang, Lingchao Cai · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.4c01898 · 被引用次数：8 · 研究领域：Radical Photochemical Reactions、Oxidative Organic Chemistry Reactions、Sulfur-Based Synthesis Techniques

Alcohols are the most commercially abundant, synthetically versatile and operationally convenient functional groups in organic chemistry. Therefore, a strategy that utilizes hydroxy-containing compounds to develop novel bond disconnection and formation process would achieve molecular diversity. Herein, a deconstructive strategy for the generation of quinoxalin-2(1H)-one derivatives has been developed from alcohol precursors via oxy-radical-induced β-fragmentation. Additionally, 1,5-HAT and deoxygenation by P(III) along with oxy-radical were demonstrated as alternative pathways for this transformation. Furthermore, with the deep-seated reorganization of a few terpenes carbon framework, a unique activity with inhibition against the growth of pathogenic fungi was observed.