北大焦宁团队:大宗化学原料利用的新突破
作者:Jianzhong Liu, Xu Qiu, Xiaoqiang Huang, Xiao Luo, Cheng Zhang, Jialiang Wei, Jun Pan, Yujie Liang, Yuchao Zhu, Qixue Qin, Song Song, Ning Jiao
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2018-11-08 00:00:56
苯胺作为重要的有机合成子和基本的化工原料,目前全球对苯胺年需求量高达500万吨以上。而环己酮作为己内酰胺和尼龙的重要前体,全球年需求量也达到500万吨。传统的工业方法需要不同的工艺分别制备这两种重要的化工产品,而且反应条件苛刻。北京大学天然及仿生药物国家重点实验室焦宁研究团队利用他们的“氮合反应”策略,创新性地实现了烷基芳烃经过碳碳键断裂引入氮原子、氧原子的新途径,同时解决了传统硝化/还原方法中富电子取代苯胺的选择性以及缺电子苯胺的合成难题,特别是首次完成了环己基苯转化为苯胺和环己酮的新反应,从而为石油产品中碳氢化合物的高附加值转化和利用开发了新的工艺。该研究开发了芳烃类大宗化工原料的新用途,通过惰性的碳碳键转化为苯胺类化合物的制备提供了新的合成思路,有望为医药、材料等领域重要的基础原料芳胺及环己酮的制备提供新策略、新工艺。
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From alkylarenes to anilines via site-directed carbon–carbon amination
作者:Jianzhong Liu, Xu Qiu, Xiaoqiang Huang, Xiao Luo, Cheng Zhang, Jialiang Wei, Jun Pan, Yujie Liang, Yuchao Zhu, Qixue Qin, Song Song, Ning Jiao
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2018-11-08 00:00:56
导语
Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.
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