Related Experiment Video
Updated: Sep 18, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Stable Vinylogous Aminal Salt as a Reactive Synthon for the Synthesis of Homologated β-Fluoroenamides
Hae Eun Lee1, Tapas R Pradhan1, Youngsuk Kim1
1Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
Abstract:
Described herein is a versatile method in which allenamide and Selectfluor are efficiently combined to produce a stable and isolable vinylogous aminal salt. This innovative salt possesses the unique ability to irreversibly convert into a reactive iminium salt at 50 °C, as evidenced by NMR spectroscopy, serving as a synthon for the synthesis of homologated β-fluoroenamides. This metal-free approach accommodates a broad range of silylated C-nucleophiles across all hybridizations as well as electron-rich (hetero)aryls, with additional functionalization further showcasing its synthetic potential.
More Related Videos
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...