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2024 , Vol. 44 >Issue 7: 2274 - 2285

DOI: https://doi.org/10.6023/cjoc202401016

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
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  • 复旦大学化学系 上海 200438

收稿日期: 2024-01-15

  修回日期: 2024-03-28

  网络出版日期: 2024-04-10

基金资助

国家自然科学基金(21971042)

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

  • Shuyu Meng ,
  • Wentao Guo ,
  • Quanrui Wang
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  • Department of Chemistry, Fudan University, Shanghai 200438
* E-mail:

Received date: 2024-01-15

  Revised date: 2024-03-28

  Online published: 2024-04-10

Supported by

National Natural Science Foundation of China(21971042)

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摘要

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

本文引用格式

孟书玉 , 郭闻涛 , 王全瑞 . 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[J]. 有机化学, 2024 , 44(7) : 2274 -2285 . DOI: 10.6023/cjoc202401016

Abstract

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

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