Ac2O-Mediated Dearylacetylative Dimerization of 2‑Arylacetyl-1-naphthols: Synthesis of Naphtho[1,2‑b]furan-3-ones

Ac2O-Mediated Dearylacetylative Dimerization of 2‑Arylacetyl-1-naphthols: Synthesis of Naphtho[1,2‑b]furan-3-ones

A novel and efficient route for the synthesis of 2-aryl-2-naphthyl naphtho­[1,2-b]­furan-3-ones is described via NaH/Ac2O-mediated dearylacetylative dimerization of 2-arylacetyl-1-naphthols in refluxing THF under open-flask conditions. A plausible mechanism is also proposed and discussed. Various re...

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Veröffentlicht in:Journal of organic chemistry 2020-03, Vol.85 (5), p.3605-3616
Hauptverfasser: Chang, Meng-Yang, Chen, Kuan-Ting, Hsiao, Yu-Ting, Chen, Shin-Mei
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel and efficient route for the synthesis of 2-aryl-2-naphthyl naphtho­[1,2-b]­furan-3-ones is described via NaH/Ac2O-mediated dearylacetylative dimerization of 2-arylacetyl-1-naphthols in refluxing THF under open-flask conditions. A plausible mechanism is also proposed and discussed. Various reaction conditions are investigated for one-pot transformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03298