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Metal-Free Intramolecular [3+2] Cycloaddition of γ‑Hydroxy Acetylenic Ketones with Alkynes for the Synthesis of Naphtho[1,2‑c]furan-5-ones and Its Derivatization via a Selective C(sp2)–H Deuteration Reaction

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journal contribution
posted on 25.05.2021, 15:35 by Si-Si Ning, Dan Meng, Jie-Yun Zhang, Shi-Lei Liu, Ni-Ni Zhou, Xiaojie Jin, Hai-Tao Zhu
A metal-free intramolecular [3+2] cycloaddtion has been achieved by treating benzene-linked propynol-ynes with AcOH/H2O in a one-pot manner. The reaction provides greener, 100% atom-economic, highly regioselective, and more practical access to functionalized naphtho­[1,2-c]­furan-5-ones with valuable and versatile applications. The regioselective α-deuteration of naphtho­[1,2-c]­furan-5-ones has been also presented with excellent deuterium incorporation and chemical yields. Moreover, the fluorescent properties of naphtho­[1,2-c]­furan-5-one products have been investigated in solution.