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Updated: Feb 17, 2026
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes
Juzeng An1, Adriano Parodi1, Magda Monari1
1Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum, Università di Bologna, Via Selmi 2, 40126, Bologna, Italy.
Abstract:
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.
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