Diastereoselective Synthesis of CF<sub>3</sub>-Dihydrobenzo[<i>k</i>]phenanthridones via Radical-Promoted Annulation of CF<sub>3</sub>-Alkenyl Quinolones with Aldehydes
A diastereoselective, radical-promoted annulation of CF<sub>3</sub>-alkenyl quinolones with aldehydes has been achieved, providing efficient access to trifluoromethyl carbinol-functionalized dihydrobenzo[<i>k</i>]phenanthridinones. Acyl radicals, generated in situ from the aldehydes in the presence of di-<i>tert</i>-butyl peroxide (DTBP), promote this annulation. The reaction proceeds under metal-free conditions and exhibits excellent functional group tolerance. The CF<sub>3</sub> group exerts a strong steric influence, leading to exclusive diastereoselectivity. The practicality of this protocol is demonstrated through the construction of furan-fused dihydrobenzo[<i>k</i>]phenanthridinone.
Authors
- Nagender Punna (ORCID: https://orcid.org/0000-0003-2761-6078)
- Jaggaraju Prudhviraj
- Jagadeesh Babu Nanubolu
- Eswar Krishna Balakandu
Institutions
- Veterinary and Agrochemical Research Centre (BE)
- Fluorochem (United States) (US)
- Indian Institute of Chemical Technology (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-08-25
- DOI
- https://doi.org/10.1021/acs.joc.5c01163
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00