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Deoxygenation of tertiary and secondary benzylic alcohols into alkanes with triethylsilane catalyzed by solid acid tin(IV) ion-exchanged montmorillonite
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2014-05-21 , DOI: 10.1016/j.tetlet.2014.05.042
Michael Andreas Tandiary , Yoichi Masui , Makoto Onaka

We discovered an efficient protocol for the conversion of tertiary and secondary benzylic alcohols into the corresponding alkanes in good to quantitative yields by employing tin(IV) ion-exchanged montmorillonite (Sn-Mont) as a solid acid catalyst and Et3SiH as the hydride source. The reaction is likely to proceed via the SN1-type reaction mechanism, that is, the formation of carbenium ions, followed by the addition of a hydride from the silane. The work-up of the reaction only requires simple filtration of the solid acid without any neutralization of the acid catalyst.



中文翻译:

固体酸锡(IV)离子交换蒙脱土催化的三乙基硅烷将叔和仲苄醇脱氧成烷烃

我们发现了一种有效的方案,可将锡(IV)离子交换的蒙脱石(Sn-Mont)作为固体酸催化剂,并将Et3SiH作为氢化物源,从而将叔和仲苄醇以良好的定量产率转化为相应的烷烃。该反应可能是经由S进行Ñ 1型反应机制,即,碳正离子的形成,随后加入来自硅烷氢化物。反应的后处理仅需要简单地过滤固体酸而不中和酸催化剂。

更新日期:2014-05-21
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