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

Autor:	Kanganavaree C; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand., Kantarod K; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand., Worakul T; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand., Soorukram D; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Kuhakarn C; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Chakarawet K; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand., Wattanathana W; Department of Materials Engineering, Faculty of Engineering, Kasetsart University, Bangkok 10900, Thailand., Surawatanawong P; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Reutrakul V; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Leowanawat P; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2024 Oct 18; Vol. 89 (20), pp. 15083-15090. Date of Electronic Publication: 2024 Oct 06.
DOI:	10.1021/acs.joc.4c01747
Abstrakt:	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.
Databáze:	MEDLINE
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