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Updated: Jun 11, 2025
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes
Chaipot Kanganavaree1, Kritchasorn Kantarod1, Thanapat Worakul1
1Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.
Abstract:
A palladium-catalyzed [3 + 2] annulation of naphthalic anhydrides with internal alkynes has been developed. The present protocol offers an efficient and convenient route to access a series of 1,2-disubstituted acenaphthylenes with excellent functional group compatibility. The reaction is proposed to proceed through a double decarboxylation sequence. The reported synthetic protocols can be extended to napthalene- and perylenedicarboximide-containing substrates. The molecular structures, photophysical properties, and frontier molecular orbitals of the obtained adducts were investigated by X-ray crystallography, UV-vis and fluorescence spectroscopy, and DFT calculations.
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