Cu-catalyzed C(sp2)–N-bond coupling of boronic acids and cyclic imides,Chemical Communications

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Cu-catalyzed C(sp2)–N-bond coupling of boronic acids and cyclic imides
Chemical Communications ( IF 4.3 ) Pub Date : 2021-10-19 , DOI: 10.1039/d1cc04356k
Linn Neerbye Berntsen ₁ , Thomas Nordbø Solvi ₁ , Kristian Sørnes ₁ , David S Wragg ₁ , Alexander H Sandtorv ₁

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A general Cu-catalyzed strategy for coupling cyclic imides and alkenylboronic acids by forming C(sp²)–N-bonds is reported. The method enables the practical and mild preparation of (E)-enimides. A large range of cyclic imides are allowed, and di- and tri-substituted alkenylboronic acids can be used. Full retention was observed in the configuration of the alkene double bond in the coupled products. The method is also applicable for preparing N-arylimides, using arylboronic acids as coupling partners. The usefulness of this strategy is exemplified by the convenient derivatization of the chemotherapy medication 5-flurouracil, the nucleoside uridine and the anti-epileptic drug phenytoin.

中文翻译：

Cu催化的硼酸和环状酰亚胺的C(sp2)-N键偶联

报道了通过形成 C(sp ² ) - N-键来偶联环状酰亚胺和烯基硼酸的一般铜催化策略。该方法能够实现（E）-烯酰亚胺的实用且温和的制备。允许使用大范围的环状酰亚胺，并且可以使用二取代和三取代的烯基硼酸。在偶联产物中烯烃双键的构型中观察到完全保留。该方法也适用于以芳基硼酸为偶联剂制备N-芳基酰亚胺。化疗药物 5-氟尿嘧啶、核苷尿苷和抗癫痫药物苯妥英的方便衍生化证明了该策略的有效性。

更新日期：2021-10-26

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