Organic Letters· 2026Q1
Polarity-Matched Formal [1 + 4] Annulation of Fluoroalkyl Hydrazonoyl Halides with α-Halo Hydrazone-Derived Azoalkenes
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- 2026year
Short summary
A new base-promoted reaction enables the formal [1 + 4] annulation of fluoroalkyl hydrazonoyl halides with α-halo acylhydrazone-derived azoalkenes, yielding CF2H- and CF3-substituted pyrazolines.
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Key points
- Developed a base-promoted formal [1 + 4] annulation reaction.
- Utilizes fluoroalkyl hydrazonoyl halides and α-halo acylhydrazone-derived azoalkenes as starting materials.
- Successfully synthesizes CF2H- and CF3-substituted pyrazolines.
- Elucidates a stepwise, polarity-matched C–C bond-forming/cyclization mechanism supported by experimental and computational data.
AI-generated from the title and abstract; the full text is not read.
Abstract
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.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Pharmaceutical Science
Pharmaceutical SciencePharmacology, Toxicology and Pharmaceutics