I₂‑Promoted Selective Oxidative Cross-Coupling/Annulation of 2‑Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1‑<i>b</i>]furan-1(2<i>H</i>)‑ones with a Quaternary Center

A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3­(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel–Crafts/oxidation/cyclization mechanism was proposed.本研究实现了一种高效且具有选择性的、以分子碘（molecular iodine）介导的2-萘酚（2-naphthols）与甲基酮（methyl ketones）之间的氧化交叉偶联/环化反应。该反应成功在3(2H)-呋喃酮（3(2H)-furanones）骨架中构建了全新的季碳中心（quaternary carbon center）。我们的合成策略提供了一条基于原位碘化（in situ iodination）的氧化偶联路径。基于实验结果，我们提出了一套自序列式的碘化/孔布姆氧化（Kornblum oxidation）/傅-克反应（Friedel–Crafts）/氧化/环化反应机理。