Improved Syntheses of Halogenated Benzene-1,2,3,4-Tetracarboxylic Diimides
Improved Syntheses of Halogenated Benzene-1,2,3,4-Tetracarboxylic Diimides
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卤代苯-1,2,3,4-四羧基二酰亚胺的改进合成
DOI：
10.1021/acs.joc.2c01241
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发表时间：
2022
期刊：
影响因子：
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通讯作者：
Cao, Dennis D.
中科院分区：
文献类型：
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作者：
Zou, Brian;Stellmach, Kellie A.;Luo, Stella M.;Gebresilassie, Feven L.;Jung, Healeam;Zhang, Cathy K.;Bass, Adam D.;Janzen, Daron E.;Cao, Dennis D.
卤代苯-1，2，3，4-四羧酸二酰亚胺衍生物的制备具有挑战性，因为可能存在竞争性的不正确环化和SNAr反应性。在这里，我们证明，绕过传统的环状酸酐，而不是直接反应二卤代苯-1，2，3，4-四羧酸与伯胺在乙酸溶剂中成功地提供了一系列的良好的产率的邻二酰亚胺产品。此外，我们表明，空间上的挑战N-衍生化可以很容易地实现微波反应器条件下。这里描述的卤代二酰亚胺是有机材料化学的有吸引力的结构单元。
The preparation of halogenated benzene-1,2,3,4-tetracarboxylic diimide derivatives is challenging because of the possibility of competitive incorrect cyclizations and SNAr reactivity. Here, we demonstrate that bypassing traditional cyclic anhydrides and instead directly reacting dihalobenzene-1,2,3,4-tetracarboxylic acids with primary amines in acetic acid solvent successfully provides a range of desirableortho-diimide products in good yields. Furthermore, we demonstrate that sterically challengingN-derivatizations can be readily achieved under microwave reactor conditions. The halogenated diimides described here are attractive building blocks for organic materials chemistry.