Related Experiment Video
Updated: Aug 9, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
α‑Fluoronitroalkenes as Fluorinated Building Blocks: Solvent-Controlled Functionalization with Hydrazones
Matthew A Saucier1, Hamdan Alrefaei1,2, Peggy A McCluggage1
1Department of BioMolecular Sciences, University of Mississippi, University, Mississippi 38677, United States.
None:
While α-fluoronitroalkenes have been widely explored in annulation and cycloaddition chemistry, controlled intermolecular C-N bond formation through conjugate addition remains largely undeveloped. Moreover, solvent-controlled divergence between conjugate addition and cyclization from identical starting materials has not been systematically demonstrated for α-fluoronitroalkenes. Herein, we report a base-mediated 1,4-conjugate addition of hydrazones to α-fluoronitroalkenes under aprotic conditions, affording N-fluoroalkyl hydrazones. In contrast, protic acidic conditions divert reactivity toward 4-fluoropyrazole formation, highlighting a solvent-controlled divergence in reaction pathways. This one-pot protocol tolerates a wide range of aromatic, heteroaromatic, and aliphatic substrates, providing isolable N-fluoroalkyl hydrazones in moderate to high yields. This study expands the synthetic utility of both hydrazones and α-fluoronitroalkenes as building blocks of interest for applications in organic synthesis and medicinal chemistry.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution: –OH and –H
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Base-Promoted α-Halogenation of Aldehydes and Ketones
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview