Zhu Liangbo, Cheng Liang, Zhang Yuxi, Xie Rugang, You Jingsong
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People's Republic of China.
J Org Chem. 2007 Apr 13;72(8):2737-43. doi: 10.1021/jo062059f. Epub 2007 Mar 10.
New (S)-pyrrolidinylmethylimidazole ligands (4a-c) have been readily synthesized in a straightforward fashion from least expensive starting materials in short steps in high yields. Relatively mild and highly efficient CuI-catalyzed N-arylation procedures for imidazoles with aryl and heteroaryl bromides or chlorides have been developed in the presence of 4a and Cs2CO3. It is important to note that the protocol could tolerate functional groups such as ester, nitrile, nitro, ketone, free hydroxyl, and free primary amine on the aryl halide. The protocol could also be applicable to other pi-electron-rich nitrogen heterocycles (pyrrole, pyrazole, indole, benzimidazole, and triazole), affording the N-arylazoles in good to excellent yields.
新型（S）-吡咯烷基甲基咪唑配体（4a - c）已通过简单的方式，以低成本起始原料，经短步骤、高收率轻松合成。在4a和碳酸铯存在下，已开发出相对温和且高效的碘化亚铜催化的咪唑与芳基和杂芳基溴化物或氯化物的N - 芳基化方法。需要注意的是，该方案能够耐受芳基卤化物上的酯、腈、硝基、酮、游离羟基和游离伯胺等官能团。该方案也可适用于其他富π电子的氮杂环（吡咯、吡唑、吲哚、苯并咪唑和三唑），以良好至优异的收率得到N - 芳基唑类化合物。
