Related Experiment Video
Updated: Jun 10, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
DMTSF-mediated electrophilic cyclization for the synthesis of 3-thiomethyl-substituted benzo[b]furan derivatives
Declan T McGurk1, Langley E Knighten1, Maria J Peña Bú2
1Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. tkesharwani@uwf.edu.
Abstract:
Benzofuran is an important backbone for molecules that make up several pharmaceuticals, herbicides/pesticides, and organo-electronics. An environmentally benign dimethyl(methylthio)sulfonium tetrafluoroborate salt was used as an electrophile to induce cyclization of o-alkynyl anisoles to form 2,3-disubstituted benzofurans. The cyclization is performed at ambient reaction conditions, only takes 12 hours to get excellent yields, and shows a high tolerance for various substituted alkynes. Also, a sulfurmethyl group obtained after the cyclization reactions allows for a cascade cyclization, and an alkyne is used in the reaction to create a thieno[3,2-b]benzofuran core structure.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition

