Straightforward Sulfonamidation via Metabisulfite-Mediated Cross Coupling of Nitroarenes and Boronic Acids under Transition-Metal-Free Conditions

被引:33
|
作者
Li, Yaping [1 ]
Wang, Ming [1 ]
Jiang, Xuefeng [1 ,2 ]
机构
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
Sulfonamide; Sodium metabisulfite; Sulfur dioxide; Nitroarene; Transition-metal-free; SULFUR-DIOXIDE; CONSTRUCTION; AMINES; DRUG;
D O I
10.1002/cjoc.202000198
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Summary of main observation and conclusion A straightforward multicomponent sulfonamidation of nitroarenes, sodium metabisulfite and boronic acids was established under transition-metal-free conditions to access diverse sulfonamides from readily available and low-cost materials modularly. Inorganic salt sodium metabisulfite not only served as a sulfur dioxide source, but also played a key role for both activator and reductant during sulfonamidation. Notably, naturally occurring biomolecules and pharmaceuticals with multiple heteroatoms and sensitive functional groups were intensively investigated in this transformtion providing versatile sulfonamides collectively. Further mechanistic studies demonstrated that nitrosoarene is the key intermediate, and the activation of boronic acid is the rate-determining step in the transformation.
引用
收藏
页码:1521 / 1525
页数:5
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