Recent Progress in Catalytic Aromatic Trifluoromethylation
Recent Progress in Catalytic Aromatic Trifluoromethylation
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DOI：
10.1002/chin.201206238
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发表时间：
2012-02
期刊：
影响因子：
--
通讯作者：
H. Amii
中科院分区：
文献类型：
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作者：
H. Amii
三氟甲基化芳香族化合物是在各种工业领域中相当感兴趣的物质。三氟甲基的高亲脂性、强吸电子能力和特征尺寸是影响其生物活性的关键因素。由于这些有吸引力的性质，三氟甲苯结构基元已被广泛用于药物、农用化学品、染料、液晶和聚合物的设计。因此，开发高效的芳香族三氟甲基化方法具有重要的科学意义和广泛的技术领域。近年来，在过渡金属催化下选择性地将三氟甲基引入芳环的研究受到了广泛的关注。本文综述了芳香族化合物的亲电和自由基三氟甲基化反应、卤代芳烃与CF3Cu试剂的交叉偶联反应、铜和钯配合物催化卤代芳烃与亲核三氟甲基化试剂的交叉偶联反应以及有效地催化氧化交叉偶联反应合成三氟甲基化芳香族化合物的成功实例。
Trifluoromethylated aromatic compounds are the substances of considerable interest in various industrial fields. The high lipophilicity, strong electron-withdrawing ability, and charasteristic size of trifluoromethyl group are key influences in biologically active molecules. Due to these attractive properties, the benzotrifluoride structural motifs have been widely employed in the design of pharmaceuticals, agrochemicals, dyes, liquid crystals, and polymers. Therefore, the development of highly efficient methodologies for aromatic trifluoromethylation is of significant importance for wide fields of science and technology. Recently, a great deal of attention has been paid to transition metal-catalyzed protocols to introduce trifluoromethyl groups into aromatic rings selectively. This review outlines the successful examples on catalytic aromatic trifluoromethylation, such as electrophilic and radical trifluoromethylation of aromatic compounds, cross-coupling of aryl halides with CF3Cu reagents, cross-coupling of aromatic halides with nucleophilic trifluoromethylation agents catalyzed by copper and palladium complexes, and catalytic oxidative cross-coupling to give trifluoromethylated aromatics effectively.