Synergistic Acid-Catalyzed Synthesis of N-Aryl-Substituted Azacycles from Anilines and Cyclic Ethers

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• 作者：Zhenbei Zhang ; Chengxia Miao ; Chungu Xia ; Wei Sun
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 1, 2016
• 年：2016
• 卷：18
• 期：7
• 页码：1522-1525
• 全文大小：373K
• ISSN：1523-7052

文摘

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.