Synergistic Acid-Catalyzed Synthesis of N-Aryl-Substituted Azacycles from Anilines and Cyclic Ethers.
Synergistic Acid-Catalyzed Synthesis of N-Aryl-Substituted Azacycles from Anilines and Cyclic Ethers.
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DOI：
10.1021/acs.orglett.6b00157
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发表时间：
2016-03
期刊：
影响因子：
5.2
通讯作者：
Zhenbei Zhang;Chengxia Miao;C. Xia;Wei Sun
中科院分区：
文献类型：
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作者：
Zhenbei Zhang;Chengxia Miao;C. Xia;Wei Sun
本文介绍了一种由芳胺和环醚合成N-芳基取代氮杂环化合物的不含金属的有效方法。在该合成中，刘易斯酸和布朗斯特酸之间的协同效应对于环醚的开环和随后的环化至关重要。B（C6 F5）3的使用使得能够从反应物形成受抑的刘易斯对（FLP），并且所得到的FLP允许通过进一步环化以中等至良好的产率容易地获得N-芳基氮杂环。水是反应产生的唯一废物，因此使其成为一个环境友好的过程。
A metal-free and efficient approach to N-aryl-substituted azacycles from arylamines and cyclic ethers is described. In this synthesis, the synergistic effect between Lewis and Brønsted acids is crucial to the ring-opening of cyclic ethers and the subsequent cyclization. The use of B(C6F5)3 enabled the formation of frustrated Lewis pairs (FLPs) from the reactants, and the resulting FLPs allowed ready access to the N-arylazacycles in moderate to good yields via further cyclization. Water is the sole waste resulting from the reaction, thereby making it an environmentally benign process.