Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 594-602.DOI: 10.6023/cjoc202507003 Previous Articles     Next Articles

ARTICLES

炔基亚砜的分子内交叉偶联/[3,3]-硫鎓离子重排策略构建环烷并[c]呋喃

郭闻涛, 孟书玉, 王全瑞*()   

  1. 复旦大学化学系 上海 200438
  • 收稿日期:2025-07-02 修回日期:2025-08-24 发布日期:2025-10-13
  • 通讯作者: 王全瑞
  • 基金资助:
    国家自然科学基金(21971042)

Intramolecular Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides for the Construction of Cycloalkano[c]furans

Wentao Guo, Shuyu Meng, Quanrui Wang*()   

  1. Department of Chemistry, Fudan University, Shanghai 200438
  • Received:2025-07-02 Revised:2025-08-24 Published:2025-10-13
  • Contact: Quanrui Wang
  • Supported by:
    National Natural Science Foundation of China(21971042)

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.

Key words: 3,3]-rearrangement, sulfonium ion, heterocyclization, cycloalkano[c]furan, intramolecular reaction