有机化学 ›› 2024, Vol. 44 ›› Issue (7): 2274-2285.DOI: 10.6023/cjoc202401016 上一篇    下一篇

研究论文

基于炔基亚砜与炔酰胺/炔醚的交叉偶联/[3,3]-硫鎓离子重排串联策略构筑四取代呋喃

孟书玉, 郭闻涛, 王全瑞*()   

  1. 复旦大学化学系 上海 200438
  • 收稿日期:2024-01-15 修回日期:2024-03-28 发布日期:2024-04-10
  • 基金资助:
    国家自然科学基金(21971042)

Cascade Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides and Ynamides/Ynol Ethers to Construct Tetrasubstituted Furans

Shuyu Meng, Wentao Guo, Quanrui Wang()   

  1. Department of Chemistry, Fudan University, Shanghai 200438
  • Received:2024-01-15 Revised:2024-03-28 Published:2024-04-10
  • Contact: E-mail: qrwang@fudan.edu.cn
  • Supported by:
    National Natural Science Foundation of China(21971042)

报道了一种无需过渡金属催化的四取代呋喃类化合物的合成策略. 在三氟化硼乙醚络合物的作用下, 炔基亚砜与炔酰胺或炔醚发生反应, 经交叉偶联、[3,3]-硫鎓离子重排和5-exo-dig杂环化关环的串联步骤生成四取代呋喃. 产物中呋喃环α-位的烷硫基可通过进一步后修饰反应, 转化为所需的其它烷基或芳基取代基.

关键词: 杂环化, [3,3]-重排, 硫鎓离子, 串联反应, 四取代呋喃

A transition-metal-free strategy for the synthesis of tetrasubstituted furans is reported. Promoted by boron trifluoride diethyl etherate, the reaction of alkynyl sulfoxides with ynamides/ynol ethers proceeded via a cascade process including cross-coupling of the two reactants, [3,3]-sulfonium rearrangement, and 5-exo-dig heterocyclization, leading to tetrasubstituted furan products. The resultant α-alkylthio groups can be used for further functionalization, such as to introduce other alkyl/aryl groups.

Key words: heterocyclization, [3,3]-rearrangement, sulfonium ion, tandem reaction, tetrasubstituted furan