Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents
One-pot direct regiodivergent annulations of chalcones, as exemplified by the drug metochalcone and a bioactive dichloro-substituted chalcone with a quinoline ring, to indanones and indenones are conveniently achieved with single-carbon reagent Kukhtin-Ramirez adducts. A Cs<sub>2</sub>CO<sub>3</sub>-promoted unusual selective cleavage of the cyclopropyl C-C bond distal to the strong carbonyl acceptor, further driven to completion by follow-up regiodivergent annulations via Pd(OAc)<sub>2</sub>-catalyzed Heck reaction or Cs<sub>2</sub>CO<sub>3</sub>-mediated S<sub>N</sub>Ar process, is key for the success.
Authors
- Xinchi Gong
- Sunewang Rixin Wang (ORCID: https://orcid.org/0000-0002-7099-2928)
Institutions
- East China Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-17
- DOI
- https://doi.org/10.1021/acs.joc.5c00497
- Citations
- 1
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- East China Normal University
- Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning