Synthesis of polysubstituted naphthalenes from cyclopentadienones using o-diiodobenzene/NaH as a benzyne system

We present an efficient strategy for constructing polysubstituted naphthalenes through Diels-Alder cycloaddition between cyclopentadienone derivatives and benzynes. Utilizing o-diiodobenzene as a stable benzyne precursor in combination with sodium hydride (NaH) enables facile in situ generation of reactive benzyne intermediate. The method features operational simplicity, use of readily accessible and cost-effective raw materials and tolerance towards diverse functional groups, thereby establishing an environmentally benign platform for synthesizing polycyclic aromatic architectures with potential applications in materials science and pharmaceutical chemistry.