Copper-catalyzed N-arylation of imidazoles and benzimidazoles
Copper-catalyzed N-arylation of imidazoles and benzimidazoles
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DOI：
10.1021/jo070807a
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发表时间：
2007-08-03
影响因子：
3.6
通讯作者：
Buchwald, Stephen L.
中科院分区：
文献类型：
--
作者：
Altman, Ryan A.;Koval, Erica D.;Buchwald, Stephen L.
4,7-二甲氧基-1,10-菲罗啉（L1c）是铜催化咪唑和苯并咪唑在温和条件下与芳基碘化物和溴基进行n -芳基化反应的有效配体。进一步的优化表明，聚乙二醇的加入加速了这一反应。各种阻碍和功能化的咪唑、苯并咪唑和芳基卤化物都得到了很好的转化。杂芳基卤化物偶联也有中高产量。我们还介绍了一系列偶联反应的结果，这些结果直接比较了L1c与其他最近报道的配体的使用。
4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.