One-Pot Assembly of Dihydrofluoren-3-ones via Intramolecular Annulation of Alkynyl-Alkynones: A Way to Functionalized Fluorenes
Herein, we reveal an approach for the synthesis of a unique structural framework, dihydrofluoren-3-one, from the reaction of propargylic alcohol with alkynyl silyl enol ether. The transformation proceeds through acid-catalyzed propargylation of silyl enol ether leading to alkynyl-alkynones and subsequent intramolecular annulation (3+2 cycloaddition) in the presence of PPh<sub>3</sub>AuNTf<sub>2</sub> (2 mol %). This novel dihydrofluoren-3-one motif was found to be a versatile precursor to provide diverse functionalized fluorenes.
Authors
- Chada Raji Reddy (ORCID: https://orcid.org/0000-0003-1491-7381)
- Shiva Kumar Kota Balaji
- René Grée (ORCID: https://orcid.org/0000-0001-8615-6126)
- Ankita Kumari (ORCID: https://orcid.org/0000-0002-9988-9027)
- Adla Vijender
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut des Sciences Chimiques de Rennes (FR)
- Indian Institute of Chemical Technology (IN)
- Université de Rennes (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-18
- DOI
- https://doi.org/10.1021/acs.joc.5c01964
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00