Site-Selective C6-β-Aminoalkylation of Tetrahydroquinolines with <i>N</i> -Arylsulfonyl Aryl Aziridines in Hexafluoroisopropanol: A Modular Approach to C6-Alkylated Quinolines
We report a metal-free method for the site-selective C6-β-aminoalkylation of tetrahydroquinolines using <i>N</i>-arylsulfonyl aziridines in HFIP at room temperature. HFIP activates aziridines through hydrogen bonding, promoting a regioselective S<sub>N</sub>2-type ring opening. The method features broad functional group tolerance, high yields (up to 89%), and full stereochemical fidelity with chiral aziridines. Gram-scale synthesis with solvent recovery highlights its practicality, while postsynthetic oxidation provides direct access to C6-alkylated quinolines.
Authors
- Murat Aslan (ORCID: https://orcid.org/0000-0001-9251-1462)
- Yunus Taskesenligil (ORCID: https://orcid.org/0000-0002-5399-2520)
- Nurullah Saracoglu
Institutions
- Biotechnology Institute (US)
- Ankara University (TR)
- Atatürk University (TR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-01-09
- DOI
- https://doi.org/10.1021/acs.joc.5c02643
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00