Stable Vicinal Bisketene Equivalents for Aryne Diels–Alder Reactions
Abstract
-butyldimethylsilyloxy)thiophenes are introduced as bench-stable Diels-Alder dienes for reaction with arynes as dienophiles. Ring-opening of the cycloadducts can be achieved via TBAF-promoted desilylation, providing convergent redox-neutral access to a library of substituted naphthoquinones. Strategically, this two-step sequence represents the application of stable vicinal bisketene equivalents as Diels-Alder dienes. Extension to anthraquinone is also demonstrated, in this case via mild autoxidation of a readily accessible cyclohexenyl-fused derivative.
Fields of Study & Subjects
Cyclization and Aryne Chemistry
Organic Chemistry Cycloaddition Reactions
Synthesis and characterization of novel inorganic/organometallic compounds
Publication details
- Journal / source
- Synlett
- Publisher
- Georg Thieme Verlag KG
- Volume
- 37
- Issue
- 10
- Pages
- 1124–1128
- Publication date
- 15 January 2026
- Language
- EN