Direct C-N Coupling of Imidazoles with Aromatic and Benzylic Compounds via Electrooxidative C-H Functionalization
Direct C-N Coupling of Imidazoles with Aromatic and Benzylic Compounds via Electrooxidative C-H Functionalization
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DOI：
10.1021/ja501093m
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发表时间：
2014-03-26
影响因子：
15
通讯作者：
Yoshida, Jun-ichi
中科院分区：
文献类型：
--
作者：
Morofuji, Tatsuya;Shimizu, Akihiro;Yoshida, Jun-ichi
发展了一种基于芳香族和苄基化合物的电氧化C-H官能化的咪唑类化合物的C-N偶联方法。成功的关键是形成作为初始产物的受保护的咪唑鎓离子，避免过氧化。在非氧化条件下脱保护得到N-取代的咪唑。各种官能团与本发明的转化相容。为了证明该方法的功效，合成了P450 17抑制剂和具有N-取代咪唑结构的抗真菌剂。
A method for the C-N coupling of imidazoles based on electrooxidative C-H functionalization of aromatic and benzylic compounds has been developed. The key to the success is the formation of protected imidazolium ions as initial products, avoiding overoxidation. Deprotection under nonoxidative conditions affords N-substituted imidazoles. Various functional groups are compatible with the present transformation. To demonstrate the power of the method, a P450 17 inhibiter and an antifungal agent having N-substituted imidazole structures were synthesized.