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Green hydrothiolation of dialkyl azodicarboxylates
Environmental Chemistry Letters ( IF 15.0 ) Pub Date : 2020-03-17 , DOI: 10.1007/s10311-020-00980-4
Maura L. Bruckchem Peixoto , Isadora S. Lermen , Fabiane Gritzenco , Benhur Godoi , Carlos E. Bencke , Marcelo Godoi

Hydrothiolations are the most useful and atom-economical pathway for the generation of sulfur–carbon and sulfur–nitrogen bonds. In particular, the preparation of sulfenylhydrazines-1,2-dicarboxylates by sulfur functionalization of nitrogen–nitrogen double bonds has received great interest in organic synthesis of compounds of unique biological properties. Previous protocols have drawbacks such as long reaction times and the use of toxic solvents. Here, we describe the preparation of sulfenylhydrazines-1,2-dicarboxylates by hydrothiolation of dialkyl azodicarboxylates under neat conditions. This new eco-friendly methodology afforded the products in up to 99% yield, in only 5 min at room temperature. A possible reaction mechanism is proposed.



中文翻译:

偶氮二羧酸二烷基酯的绿色氢硫醇化

氢硫基化是生成硫-碳和硫-氮键的最有用和最经济的途径。特别是,通过氮-氮双键的硫官能化制备亚磺酰肼-1,2-二羧酸酯对有机合成具有独特生物学特性的化合物引起了极大兴趣。先前的协议具有诸如反应时间长和使用有毒溶剂的缺点。在这里,我们描述了在纯净条件下通过偶氮二羧酸二烷基酯的氢硫醇化制备亚磺酰肼-1,2-二羧酸酯。这种新的环保方法在室温下仅需5分钟即可提供高达99%的产品收率。提出了一种可能的反应机理。

更新日期:2020-03-17
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