Related Experiment Video
Updated: May 26, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Three-Component Sulfonylation and Heteroannulation Enabled by 3-Fold Defluorofunctionalization of Trifluoromethyl
Shu-Ji Gao1, Xue-Ying Huang1, Xiao-Ying Li1
1Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Abstract:
Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones and biocompatible sodium sulfinates has been developed for the modular synthesis of densely functionalized furans with regio-defined C2,4-bissulfonyl and C3-trifluoromethyl substitutions. This three-component method proceeds through a sequential sulfonylation and intramolecular O-cyclization, enabling the assembly of one furan ring, the formation of C-SO2/C-O bonds, and the cleavage of three C(sp3)-F bonds in a one-pot manner under transition metal-free conditions. Moreover, the obtained furan product can further react with a benzyne precursor to generate 1,4-epoxynaphthalene through a Diels-Alder cycloaddition. The reaction is also distinguished by its broad substrate scope, excellent functional group tolerance, and scalability.
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
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation