Related Experiment Video
Updated: Feb 14, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Ring-Opening/Friedel-Crafts Cascade of Benzylcyclobutanones toward Naphthalenes
Liyan Fu1, Min Zhang1, Xiaofei Zhu1
1Department of Chemistry, Jilin Provincial Key Laboratory of Carbon Fiber Development and Application, College of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, P. R. China.
Abstract:
An unprecedented copper-catalyzed intramolecular ring-opening/Friedel-Crafts reaction of cyclobutanones is developed by judicious refinements of the substrate and reaction conditions. Distinct from previous reaction patterns, the in situ generated zwitterionic species from selective C-C bond cleavage of cyclobutanones was captured by properly installed benzyl units, delivering a variety of polysubstituted naphthalenes smoothly in up to 99% yield. The strategy is featured by the mild conditions without the employment of sensitive or stoichiometric Lewis acids, with water being the only byproduct. Besides 3-aryl cyclobutanones, 3-alkyl precursors were also proven to be compatible in the catalytic protocol. Synthesis and transformation of the reaction intermediate allowed for verification of the catalytic pathway.
Related Concept Videos
Limitations of Friedel–Crafts Reactions
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Intracellular Signaling Cascades
Rab Cascades
Amplifying Signals via Enzymatic Cascade

