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

2014-03-21T00:00:00Z (GMT) by Qinghe Gao Xia Wu Shan Liu Anxin Wu
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.