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Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2021-01-04 , DOI: 10.1016/j.tetlet.2020.152737
Olga M. Mulina , Alexey I. Ilovaisky , Till Opatz , Alexander O. Terent'ev

A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.



中文翻译:

光氧化还原催化的叠氮化物和亚磺酸盐合成N-未取代的烯胺砜

本文描述了由金属叠氮化物和亚磺酸钠以中等至高收率的无金属可见光光氧化还原催化的N-未取代的烯氨基砜的合成。该反应在乙醇中进行,并使用曙红Y作为易得的光催化剂,并与硝基苯结合用作电子穿梭物。考虑到涉及的步骤数(生成磺酰基,将其加至双键,消除分子氮并形成亚氨基自由基,然后使其还原和质子化)以及氧化还原活性反应的数量对于合作伙伴,该过程的选择性非常出色。

更新日期:2021-01-21
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