Rapid and Modular Access to Multifunctionalized 1,2-Azaborines via Palladium/Norbornene Cooperative Catalysis,Journal of the American Chemical Society

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Rapid and Modular Access to Multifunctionalized 1,2-Azaborines via Palladium/Norbornene Cooperative Catalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-03-29 , DOI: 10.1021/jacs.4c01582
Shinyoung Choi ₁ , Guangbin Dong ₁

Affiliation

1,2-Azaborines, a unique class of BN-isosteres of benzene, have attracted great interest across several fields. While significant advancements have been made in the postfunctionalization of 1,2-azaborines, challenges still exist for the selective functionalization of the C4 position and access to 1,2-azaborines with five or six independently installed substituents. Here we report a rapid and modular method for C3 and C4 difunctionalization of 1,2-azaborines using the palladium/norbornene (Pd/NBE) cooperative catalysis. Enabled by the C2 amide-substituted NBE, diverse 3-iodo-1,2-azaborines can be used as substrates, showing broad functional group tolerance. Besides ortho arylation, preliminary success of ortho alkylation has also been realized. In addition, a range of alkenes and nucleophiles can be employed for ipso C3 functionalization. The reaction is scalable, and various postfunctionalizations, including forming hexa-substituted 1,2-azaborines, have been achieved.

中文翻译：

通过钯/降冰片烯协同催化快速、模块化地获得多功能 1,2-氮杂硼烯

1,2-氮杂硼是苯的一类独特的 BN 等排体，在多个领域引起了极大的兴趣。虽然 1,2-氮杂蛋白的后功能化取得了重大进展，但 C4 位的选择性官能化和获得具有 5 个或 6 个独立安装的取代基的 1,2-氮杂蛋白仍然存在挑战。在这里，我们报道了一种使用钯/降冰片烯（Pd/NBE）协同催化对 1,2-氮杂霉烯进行 C3 和 C4 二官能化的快速模块化方法。在 C2 酰胺取代的 NBE 的支持下，多种 3-碘-1,2-氮杂硼酸可用作底物，显示出广泛的官能团耐受性。除了邻位芳基化，邻位烷基化也取得了初步成功。此外，一系列烯烃和亲核试剂可用于 ipso C3 官能团化。该反应是可扩展的，并且已经实现了各种后功能化，包括形成六取代的 1,2-氮杂花硼酸。

更新日期：2024-03-29

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