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Synthesis of unsymmetrically substituted triarylamines via acceptorless dehydrogenative aromatization using a Pd/C and p-toluenesulfonic acid hybrid relay catalyst
Chemical Science ( IF 8.4 ) Pub Date : 2020-03-25 , DOI: 10.1039/c9sc06442g
Satoshi Takayama 1, 2, 3, 4, 5 , Takafumi Yatabe 1, 2, 3, 4, 5 , Yu Koizumi 1, 2, 3, 4, 5 , Xiongjie Jin 2, 3, 4, 5, 6 , Kyoko Nozaki 2, 3, 4, 5, 6 , Noritaka Mizuno 1, 2, 3, 4, 5 , Kazuya Yamaguchi 1, 2, 3, 4, 5
Affiliation  

An efficient and convenient procedure for synthesizing triarylamines based on a dehydrogenative aromatization strategy has been developed. A hybrid relay catalyst comprising carbon-supported Pd (Pd/C) and p-toluenesulfonic acid (TsOH) was found to be effective for synthesizing a variety of triarylamines bearing different aryl groups starting from arylamines (diarylamines or anilines), using cyclohexanones as the arylation sources under acceptorless conditions with the release of gaseous H2. The proposed reaction comprises the following relay steps: condensation of arylamines and cyclohexanones to produce imines or enamines, dehydrogenative aromatization of the imines or enamines over Pd nanoparticles (NPs), and elimination of H2 from the Pd NPs. In this study, an interesting finding was obtained indicating that TsOH may promote the dehydrogenation.

中文翻译:

使用Pd / C和对甲苯磺酸杂化中继催化剂通过无受体脱氢芳构化合成不对称取代的三芳基胺

已经开发了基于脱氢芳构化策略合成三芳基胺的有效且方便的方法。发现包含碳载Pd(Pd / C)和甲苯磺酸(TsOH)的杂化中继催化剂可有效地以环己酮为原料从芳基胺(二芳基胺或苯胺)合成各种带有不同芳基的三芳基胺。芳基化源在无受体条件下释放出气态H 2。拟议的反应包括以下中继步骤:芳胺和环己酮的缩合以生成亚胺或烯胺,亚胺或烯胺在Pd纳米颗粒(NPs)上的脱氢芳构化,以及消除H 2来自Pd NP。在这项研究中,获得了一个有趣的发现,表明TsOH可以促进脱氢。
更新日期:2020-03-25
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