Metal-Free Synthesis of (E)-Vinyl Sulfones via An Insertion of Sulfur Dioxide/1,5-Hydrogen Atom Transfer Sequence

被引：27
|
作者：
He, Fu-Sheng [1 ,2 ]
Yao, Yanfang [3 ]
Xie, Wenlin [3 ]
Wu, Jie [1 ,2 ,4 ]
机构：
[1] Taizhou Univ, Sch Pharmaceut & Mat Engn, 1139 Shifu Ave, Taizhou 318000, Peoples R China
[2] Taizhou Univ, Inst Adv Studies, 1139 Shifu Ave, Taizhou 318000, Peoples R China
[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 21期
基金：
中国国家自然科学基金;
关键词：
vinyl sulfones; sulfur dioxide insertion; vinyl radical; 1,5-hydrogen atom transfer; metal-free; CATALYZED ASYMMETRIC HYDROGENATION; UNACTIVATED C(SP(3))-H BONDS; VINYL SULFONES; TERMINAL ALKYNES; DIOXIDE; RADICALS; ARYLSULFONYLATION; SULFONYLATION; CONVERSION; ROUTE;
D O I：
10.1002/adsc.202000778
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A metal-free three-component reaction of propargyl alcohols, sodium metabisulfite, and aryldiazonium tetrafluoroborates under mild conditions is described. The reaction proceeds efficiently at room temperature without the need of any catalysts, affording the corresponding (E)-vinyl sulfones in moderate to good yields with excellent functional group tolerance. Preliminary mechanistic studies show that a vinyl radical-induced 1,5-hydrogen atom transfer process and functional group migration are involved, resulting in the cleavage of inert C-H and C-C bonds in sequence.
引用
收藏
页码：4744 / 4748
页数：5
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