Polarity-Matched Formal [1 + 4] Annulation of Fluoroalkyl Hydrazonoyl Halides with α-Halo Hydrazone-Derived Azoalkenes
Abstract Fluoroalkyl hydrazonoyl halides are typically used as nitrile–imine 1,3-dipole precursors, whereas their carbon-centered reactivity remains underdeveloped. Herein we report a base-promoted formal [1 + 4] annulation of α-halo acylhydrazone-derived azoalkenes with fluoroalkyl hydrazonoyl halides, providing CF2H- and CF3-substituted pyrazolines. Control experiments, time-course NMR, Fukui function/dual-descriptor analysis, and DFT calculations support a stepwise polarity-matched C–C bond-forming/cyclization pathway.
Authors
- Yulai Hu (ORCID: https://orcid.org/0000-0002-9630-4150)
- Danfeng Huang (ORCID: https://orcid.org/0000-0002-5848-1164)
- Panpan Zhou (ORCID: https://orcid.org/0000-0001-8111-8155)
- Junjiao Wang (ORCID: https://orcid.org/0000-0002-5091-5263)
- Na Li (ORCID: https://orcid.org/0000-0001-6924-8387)
- Kaijian Zhu
- Ke-Hu Wang
- Yang Li
Institutions
- Lanzhou University of Technology (CN)
- Northwest Normal University (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-09-14
- DOI
- https://doi.org/10.1021/acs.orglett.6c03186
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00