Pd-Catalyzed B–H Aryl/Alkenylation of 1,2-Azaborines

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL ACS Catalysis Pub Date : 2024-11-04 DOI:10.1021/acscatal.4c04576

Zhen Zhang, Dandan Jiang, Peiwen Su, Kai Yang, Peiyuan Yu, Qiuling Song

引用次数: 0

Abstract

Direct functionalization of 1,2-azaborines to construct B–C bonds remains challenging. Here, we report a Pd-catalyzed B–H aryl/alkenylation reaction of 1,2-azaborines. The method provides a general platform to access diverse boron-substituted 1,2-azaborine compounds (>60 examples). The synthetic utility is highlighted through the late-stage modification of bioactive molecules, as well as the preparation and transformations of the ¹⁰B-enriched 1,2-azaborine product and the synthesis of four BN isostere analogues of bioactive molecules. And the reaction mechanism is also explored and discussed.

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Pd 催化 1,2-氮杂硼烷的 B-H 芳基/烯基化反应

对 1,2-azaborines 进行直接官能化以构建 B-C 键仍然具有挑战性。在此，我们报告了一种 Pd 催化的 1,2-氮杂硼烷的 B-H 芳基/烯基化反应。该方法提供了一个通用平台，可以获得多种硼取代的 1,2-氮杂硼烷化合物（60 个实例）。通过对生物活性分子进行后期修饰，以及制备和转化 10B 富集的 1,2-氮杂硼烷产物和合成四种生物活性分子的 BN 等效类似物，突出了该方法的合成实用性。此外，还对反应机理进行了探讨和讨论。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.