Catalytic Regio- and Stereoselective Alkene Sulfenoamination for 1,4-Benzothiazine Synthesis

被引：20

作者：

Alom, Nur-E. ^{[1
,2
]}

Kaur, Navdeep ^{[1
,2
]}

Wu, Fan ^{[1
,2
]}

Saluga, Shannon Jasmine ^{[1
,2
]}

Li, Wei ^{[1
,2
]}

机构：

[1] Univ Toledo, Dept Chem & Biochem, 2801 W Bancroft St, Toledo, OH 43606 USA

[2] Univ Toledo, Sch Green Chem & Engn, 2801 W Bancroft St, Toledo, OH 43606 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 28期

关键词：

alkene sulfenoamination; 1,4-benzothiazines; heterocycles; iodide catalysis; thiiranium; ONE-POT SYNTHESIS; INTRAMOLECULAR SULFENOAMINATION; OXIDATION CHEMISTRY; C-S; IONS; DIFUNCTIONALIZATION; ACCESS; OXYAMINATION; THIAZOLINES; EPISULFIDES;

D O I：

10.1002/chem.201900549

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An alkene sulfenoamination reaction with 2-aminothiophenol is developed using iodide catalysis. This reaction renders access to useful 1,4-benzothiazines with good functional group compatibility including both electron-donating and electron-withdrawing substituents. The reaction is proposed to proceed through an inversion of the polarity of the thiol functionality. Our mechanistic studies reveal that both thiiranium and thiyl radical pathways are plausible and that the disulfide reagent can also function as a viable substrate in this reaction.

引用

页码：6902 / 6906

页数：5

共 64 条

[1] Functionalized 1,4-Benzothiazine: A Versatile Scaffold with Diverse Biological Properties [J].