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Oxidative Functionalization of Cyclic N-Arylamines with Nitromethane and TMSCN Using the T-HYDRO/t-BuOK System
Synthesis ( IF 2.6 ) Pub Date : 2017-11-06 , DOI: 10.1055/s-0036-1590943
Mariappan Periasamy , Gunda Rao

Abstract

Tertiary cyclic N-arylamines react with nitromethane in the presence of the tert-butyl hydroperoxide (T-HYDRO)/t-BuOK system to give β-nitroamines in up to 90% yield. When TMSCN is used in place of nitromethane, α-aminonitriles are obtained in up to 96% yield. The method is suitable for several unactivated cyclic arylamine substrates. These transformations are rationalized considering the formation of the corresponding iminium ion intermediates via an initial electron transfer process.

Tertiary cyclic N-arylamines react with nitromethane in the presence of the tert-butyl hydroperoxide (T-HYDRO)/t-BuOK system to give β-nitroamines in up to 90% yield. When TMSCN is used in place of nitromethane, α-aminonitriles are obtained in up to 96% yield. The method is suitable for several unactivated cyclic arylamine substrates. These transformations are rationalized considering the formation of the corresponding iminium ion intermediates via an initial electron transfer process.



中文翻译:

使用T-HYDRO / t-BuOK系统用硝基甲烷和TMSCN氧化环状N-芳基胺

摘要

丁基氢过氧化物(T-HYDRO)/ t - BuOK体系存在下,环状N-芳基叔胺与硝基甲烷反应生成β-硝基胺,收率高达90%。当使用TMSCN代替硝基甲烷时,以高达96%的产率获得α-氨基腈。该方法适用于几种未活化的环状芳基胺底物。考虑到通过初始电子转移过程形成相应的亚胺离子中间体,这些转化是合理的。

丁基氢过氧化物(T-HYDRO)/ t - BuOK体系存在下,环状N-芳基叔胺与硝基甲烷反应生成β-硝基胺,收率高达90%。当使用TMSCN代替硝基甲烷时,以高达96%的产率获得α-氨基腈。该方法适用于几种未活化的环状芳基胺底物。考虑到通过初始电子转移过程形成相应的亚胺离子中间体,这些转化是合理的。

更新日期:2017-11-06
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