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Updated: Feb 10, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Electrochemically modified Corey-Fuchs reaction for the synthesis of arylalkynes. The case of
Fabiana Pandolfi1, Isabella Chiarotto1, Marta Feroci1
1Deptartment of Fundamental and Applied Sciences for Engineering (SBAI), Sapienza University of Rome, via Castro Laurenziano, 7, 00161, Rome, Italy.
Abstract:
The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting electrolyte, the reaction can be directed towards the synthesis of the terminal alkyne (Et4NBF4) or the bromoalkyne (NaClO4). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction.
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