α-Diimine-based conjugated microporous polymers as heterogeneous ligands for highly efficient palladium-catalyzed direct C–H arylations,Polymer Chemistry

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α-Diimine-based conjugated microporous polymers as heterogeneous ligands for highly efficient palladium-catalyzed direct C–H arylations
Polymer Chemistry ( IF 4.1 ) Pub Date : 2024-07-09 , DOI: 10.1039/d4py00539b
Chang-An Wang ₁ , Ya-Ru Wang _{1,

2} , Mia Guo ₃ , Bing Han ₄ , Kun Nie ₁ , Yin-Feng Han ₁ , Feng-Shou Liu ₃

Affiliation

Direct C–H bond transformation has long been regarded as the “holy grail of chemistry” in the field of organic synthesis. Significant progress has been achieved in this area with a variety of homogeneous transition-metal catalysts. In contrast, only a few examples of heterogeneous catalysis of direct C–H bond transformation have been reported. In this work, we report the use of new types of α-diimine structure functionalized conjugated microporous polymers (DIM-CMPs) as ligands for heterogeneous catalysis, which show high efficiency and recyclability in Pd-catalyzed direct C–H arylations. These DIM-CMPs are distinguished by their exceptional stability, robust porous framework, and efficacious allocation of palladium active sites, all of which cumulatively contribute to their superior catalytic performance. The superior utility of DIM-Pd-CMPs in catalysis is elucidated by their broad substrate scope (32 examples, 82–98% yields), along with tolerance towards a variety of functional groups, good recyclability (6 times) and the ability to be performed on a gram scale (10 mmol). Moreover, their utility has been highlighted in the synthesis of potentially bioactive molecules through sequential C–H arylation and Suzuki coupling. This innovative development is poised to significantly impact the synthesis of heterobiaryls, which are crucial constituents of a variety of natural products and pharmaceutical compounds, potentially revolutionizing catalysis in industrial applications and offering significant economic and environmental advantages.

中文翻译：

基于α-二亚胺的共轭微孔聚合物作为异质配体用于高效钯催化的直接C-H芳基化

直接C-H键转化长期以来被视为有机合成领域的“化学圣杯”。各种均相过渡金属催化剂在这一领域取得了重大进展。相比之下，仅报道了一些直接 C-H 键转化的多相催化的例子。在这项工作中，我们报道了使用新型α-二亚胺结构功能化共轭微孔聚合物（DIM-CMP）作为多相催化配体，其在Pd催化的直接C-H芳基化中表现出高效率和可回收性。这些 DIM-CMP 以其卓越的稳定性、坚固的多孔框架和有效的钯活性位点分配而著称，所有这些累积起来有助于其卓越的催化性能。 DIM-Pd-CMP 在催化中的卓越效用体现在其广泛的底物范围（32 个实例，82-98% 产率）、对各种官能团的耐受性、良好的可回收性（6 次）和能够被以克规模（10 mmol）进行。此外，它们在通过连续 C-H 芳基化和 Suzuki 偶联合成潜在生物活性分子方面的实用性得到了凸显。这一创新发展将对杂联芳基化合物的合成产生重大影响，杂联芳基化合物是各种天然产物和药物化合物的关键成分，有可能彻底改变工业应用中的催化作用，并提供显着的经济和环境优势。

更新日期：2024-07-09

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