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

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

作　　者：Meng Shuyu Guo Wentao Wang Quanrui 孟书玉;郭闻涛;王全瑞(复旦大学化学系,上海200438)

机构地区：[1]Department of Chemistry,Fudan University,Shanghai 200438

出　　处：《有机化学》2024年第7期2274-2285,共12页Chinese Journal of Organic Chemistry

摘　　要：A transition-metal-free strategy for the synthesis of tetrasubstituted furans is reported.Promoted by boron trifluo-ride 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.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：HETEROCYCLIZATION [3 3]-rearrangement sulfonium ion tandem reaction tetrasubstituted furan 

分 类 号：O626.11[理学—有机化学]