Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes
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.
Authors
- Khetpakorn Chakarawet (ORCID: https://orcid.org/0000-0001-5905-3578)
- Panida Surawatanawong (ORCID: https://orcid.org/0000-0002-0300-4205)
- Chutima Kuhakarn (ORCID: https://orcid.org/0000-0003-4638-4356)
- Thanapat Worakul (ORCID: https://orcid.org/0000-0002-8031-1727)
- Darunee Soorukram (ORCID: https://orcid.org/0000-0002-6865-2270)
- Worawat Wattanathana (ORCID: https://orcid.org/0000-0002-3592-3708)
- Kritchasorn Kantarod
- Pawaret Leowanawat (ORCID: https://orcid.org/0000-0001-8745-2322)
- Vichai Reutrakul (ORCID: https://orcid.org/0000-0002-0743-1300)
- Chaipot Kanganavaree
Institutions
- Kasetsart University (TH)
- Mahidol University (TH)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-06
- DOI
- https://doi.org/10.1021/acs.joc.4c01747
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Mahidol University
- National Research Council of Thailand
- Faculty of Science, Mahidol University