Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes
Issued Date
2024-01-01
Resource Type
ISSN
00223263
eISSN
15206904
Scopus ID
2-s2.0-85205803285
Journal Title
Journal of Organic Chemistry
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Organic Chemistry (2024)
Suggested Citation
Kanganavaree C., Kantarod K., Worakul T., Soorukram D., Kuhakarn C., Chakarawet K., Wattanathana W., Surawatanawong P., Reutrakul V., Leowanawat P. Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes. Journal of Organic Chemistry (2024). doi:10.1021/acs.joc.4c01747 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/101627
Title
Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes
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Corresponding Author(s)
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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.