Related Experiment Video
Updated: Apr 14, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Coumarin-Rewired Benzothiophenes: Skeletal Editing for Peripheral Heterofunctionalization
Fu-Min Chen1, Yi-Ting Shi1, Huan Hu1
1School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
None:
A single-atom skeletal editing strategy is reported for dual-site heterofunctionalization of benzothiophenes. The transformation involves a sulfonium intermediate formed with coumarin, triggering sequential ring opening and fusion to reconstruct the benzothiophene scaffold. Strategic tuning of the reaction conditions enables the coumarin module to function as a selective benzoyl or carboxyl donor for peripheral modification. This method facilitates efficient framework remodeling and peripheral diversification, bypassing selectivity challenges inherent in conventional C-H functionalization.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
Directing and Steric Effects in Disubstituted Benzene Derivatives
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene