Related Experiment Video
Updated: Jul 16, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Defluorinative 1,3-Dienylation of Fluoroalkyl N-Triftosylhydrazones with Homoallenols
Xiaolong Zhang1, Jiahua Deng1, Yong Ji1
1Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
Abstract:
A silver-catalyzed regioselective defluorinative 1,3-dienylation of trifluoromethyl phenyl N-triftosylhydrazones using homoallenols as 1,3-dienyl sources provides a variety of α-(di)fluoro-β-vinyl allyl ketones with excellent functional group tolerance in moderate to good yields. The reaction proceeds through a silver carbene-initiated sequential etherification and Claisen type [3,3]-sigmatropic rearrangement cascade. The synthetic utility of this protocol was demonstrated through the downstream synthetic elaboration toward diverse synthetically useful building blocks.
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
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Base-Promoted α-Halogenation of Aldehydes and Ketones
Hydroboration-Oxidation of Alkenes
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions