Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes

Kanganavaree C.Kantarod K.Worakul T.Soorukram D.Kuhakarn C.Chakarawet K.Wattanathana W.Surawatanawong P.Reutrakul V.Leowanawat P.Mahidol University2024-10-172024-10-172024-01-01Journal of Organic Chemistry (2024)00223263https://repository.li.mahidol.ac.th/handle/20.500.14594/101627A 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.ChemistryPalladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal AlkynesArticleSCOPUS10.1021/acs.joc.4c017472-s2.0-8520580328515206904