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Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes

An, J., Parodi, A., Monari, M., Reis, M. C., Lopez, C. S. & Bandini, M., 11-Dec-2017, In : Chemistry - A European Journal. 23, 69, p. 17473-17477 5 p.

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  • Gold‐Catalyzed Dearomatization of 2‐Naphthols with Alkynes

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DOI

The site-selective dearomatization of naphthols is realized in a straightforward manner through a gold(I)-catalyzed [3,3]-sigmatropic rearrangement/allene functionalization cascade sequence. The method employs readily available naphthylpropargyl ethers as starting materials. A range of densely functionalized dihydrofurylnaphthalen-2(1H)-ones are obtained in high yields (up to 98 %) and extremely mild reaction conditions (reagent grade solvent, air, 10 minute reaction time). A complete theoretical elucidation of the reaction machinery is also proposed, providing a rationale for important issues such as regio- and chemoselectivity.

Original languageEnglish
Pages (from-to)17473-17477
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number69
Publication statusPublished - 11-Dec-2017
Externally publishedYes

    Keywords

  • catalysis, dearomatization, gold, mechanism, naphthol

ID: 134759408