Disilanes as oxygen scavengers and surrogates of hydrosilanes suitable for selective reduction of nitroarenes, phosphine oxides and other valuable substrates,Organic Chemistry Frontiers

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Disilanes as oxygen scavengers and surrogates of hydrosilanes suitable for selective reduction of nitroarenes, phosphine oxides and other valuable substrates
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-09-05 00:00:00 , DOI: 10.1039/c7qo00566k
Ashot Gevorgyan _{1,

2,

3,

4} , Satenik Mkrtchyan _{1,

2,

3,

4} , Tatevik Grigoryan _{1,

2,

3,

4} , Viktor O. Iaroshenko _{1,

2,

3,

4}

Affiliation

In this report, we demonstrate that the reaction of nitroarenes with hexamethyldisilane under various conditions affords a different range of compounds with excellent selectivity. In particular, the reaction of nitroarenes with hexamethyldisilane using a CsF/TBAB/toluene system provides suitable azo compounds, while in the presence of a CsF/TBAB/[Pd]/EtOH system hexamethyldisilane acts as a novel surrogate of gaseous trimethylsilane, thus, reducing nitroarenes to corresponding anilines. The synthetic value of the developed methodology was further extended by the reduction of a wide range of substrates including N-oxides, sulfoxides, phosphine oxides etc.

中文翻译：

乙硅烷作为氢硅烷的除氧剂和替代物，适用于选择性还原硝基芳烃，氧化膦和其他有价值的底物

在这份报告中，我们证明了硝基芳烃与六甲基乙硅烷在各种条件下的反应提供了具有优异选择性的不同范围的化合物。特别是，使用CsF / TBAB /甲苯系统使硝基芳烃与六甲基乙硅烷反应可提供合适的偶氮化合物，而在CsF / TBAB / [Pd] / EtOH体系存在下，六甲基乙硅烷可作为气态三甲基硅烷的新型替代物，因此，将硝基芳烃还原为相应的苯胺。通过减少包括N-氧化物，亚砜，氧化膦等在内的多种底物，进一步扩展了所开发方法的综合价值。

更新日期：2017-09-12

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