Intramolecular Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides for the Construction of Cycloalkano[ c ]furans
Abstract
An intramolecular tandem rearrangement for the synthesis of bicyclic furans is reported.The reaction was initiated by an intramolecular cross-coupling of the built-in alkynyl sulfoxide and alkynyl sulfide motifs in the presence of BF3•Et2O, followed by a [3,3]-sigmatropic sulfonium rearrangement and 5-exo-dig cyclization, affording cycloalkano[c]furans as final products in moderate yields with 100% atom economy.The synthetic utility of the resulting furans has been demonstrated through late-stage diversification by utilizing the alkylthio groups or the furan rings.
Fields of Study & Subjects
Organic Chemistry Synthesis Methods
Catalytic Alkyne Reactions
Sulfur-Based Synthesis Techniques
Publication details
- Journal / source
- Chinese Journal of Organic Chemistry
- Volume
- 46
- Issue
- 2
- Pages
- 594–594
- Publication date
- 1 January 2026
- Language
- EN