Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism

被引：129
|
作者：
Meyer, Andreas Uwe [1 ]
Strakova, Karolina [1 ]
Slanina, Tomas [1 ,2 ,3 ]
Koenig, Burkhard [1 ]
机构：
[1] Univ Regensburg, Fac Chem & Pharm, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany
[2] Masaryk Univ, Dept Chem, Kamenice 5, Brno 62500, Czech Republic
[3] Masaryk Univ, RECETOX, Kamenice 5, Brno 62500, Czech Republic
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 25期
关键词：
alkyl sulfinates; photocatalysis; reaction mechanisms; transient spectroscopy; vinyl sulfones; DOPAMINE-RECEPTOR INACTIVATION; VINYL SULFONES; VISIBLE-LIGHT; METAL-FREE; DECARBOXYLATIVE SULFONYLATION; (E)-ALKENYL SULFONES; (E)-VINYL SULFONES; MEDIATED SYNTHESIS; ORGANIC-SYNTHESIS; CINNAMIC-ACIDS;
D O I：
10.1002/chem.201601000
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Alkyl- and aryl vinyl sulfones were obtained by eosin Y (EY)-mediated visible-light photooxidation of sulfinate salts and the reaction of the resulting S-centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X-ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts.
引用
收藏
页码：8694 / 8699
页数：6
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