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A Convoluted Polyvinylpyridine‐Palladium Catalyst for Suzuki‐Miyaura Coupling and C−H Arylation
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-08-05 , DOI: 10.1002/adsc.202000742 Aya Ohno 1 , Takuma Sato 1 , Toshiaki Mase 2 , Yasuhiro Uozumi 2 , Yoichi M. A. Yamada 1
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-08-05 , DOI: 10.1002/adsc.202000742 Aya Ohno 1 , Takuma Sato 1 , Toshiaki Mase 2 , Yasuhiro Uozumi 2 , Yoichi M. A. Yamada 1
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The development of highly active and reusable supported catalysts for Suzuki‐Miyaura coupling and catalytic C−H arylation is important for fundamental and applied chemistry, with these reactions being used to produce medical compounds and functional materials. Herein, we found that a mesoporous composite made of a linear poly(4‐vinylpyridine) and tetrachloropalladate acted as a dual‐mode catalyst for a variety of cross‐coupling reactions, with both Pd nanoparticles and a Pd complex catalyst being observed under different conditions. The polyvinylpyridine‐palladium composite 1 was readily prepared via the molecular convolution of poly(4‐vinylpyridine) and sodium tetrachloropalladate to provide a hardly soluble polymer‐metal composite. The Suzuki‐Miyaura coupling and the C−H arylation of aryl chlorides and bromides with arylboronic acids, thiophenes, furans, benzene, and anisole proceeded in the presence of 0.004 mol% (40 mol ppm) to 1 mol% Pd of 1 to afford the corresponding coupling products in high yields. Furthermore, the catalyst was reused without an appreciable loss of activity. Pharmaceutical compounds and functional materials were synthesized via the coupling reactions. N2 gas adsorption/desorption analysis indicated that the catalyst had a mesoporous nature, which played a crucial role in the catalysis. In the Suzuki‐Miyaura couplings, in situ generated palladium nanoparticles in the polymer matrix were catalytically active, while a polymeric Pd(II) complex was crucial in the C−H arylations. These catalytic species were investigated via XAFS, XPS, far‐infrared absorption, and Raman spectroscopies, as well as DFT calculations.
中文翻译：
铃木宫浦联轴器和CH芳基化反应的卷积聚乙烯吡啶钯钯催化剂
开发用于铃木-宫浦偶合和催化CH芳基化的高活性和可重复使用的载体催化剂对于基础化学和应用化学至关重要，这些反应可用于生产医药化合物和功能材料。在这里，我们发现由线性聚（4-乙烯基吡啶）和四氯钯酸盐制成的介孔复合物充当多种交叉偶联反应的双模催化剂，在不同条件下观察到Pd纳米颗粒和Pd络合物催化剂。聚乙烯基吡啶钯复合材料1通过聚（4-乙烯基吡啶）和四氯钯酸钠的分子卷积可轻松制备得到难溶的聚合物-金属复合材料。铃木-宫浦耦合和芳基氯，并用芳基硼酸，噻吩，呋喃，苯溴化物的C-H芳基化，和苯甲醚在0.004摩尔％（40摩尔ppm的）存在下进行，以1摩尔％的Pd的1，得到相应的偶联产品产量高。此外，催化剂可以重复使用而没有明显的活性损失。药物化合物和功能材料通过偶联反应合成。N 2气体吸附/解吸分析表明该催化剂具有介孔性质，在催化中起关键作用。在铃木宫浦联轴器中在聚合物基体中原位生成的钯纳米粒子具有催化活性，而聚合的Pd（II）络合物对于CH芳基化至关重要。通过XAFS，XPS，远红外吸收和拉曼光谱以及DFT计算研究了这些催化物质。
更新日期：2020-08-05
中文翻译：
铃木宫浦联轴器和CH芳基化反应的卷积聚乙烯吡啶钯钯催化剂
开发用于铃木-宫浦偶合和催化CH芳基化的高活性和可重复使用的载体催化剂对于基础化学和应用化学至关重要，这些反应可用于生产医药化合物和功能材料。在这里，我们发现由线性聚（4-乙烯基吡啶）和四氯钯酸盐制成的介孔复合物充当多种交叉偶联反应的双模催化剂，在不同条件下观察到Pd纳米颗粒和Pd络合物催化剂。聚乙烯基吡啶钯复合材料1通过聚（4-乙烯基吡啶）和四氯钯酸钠的分子卷积可轻松制备得到难溶的聚合物-金属复合材料。铃木-宫浦耦合和芳基氯，并用芳基硼酸，噻吩，呋喃，苯溴化物的C-H芳基化，和苯甲醚在0.004摩尔％（40摩尔ppm的）存在下进行，以1摩尔％的Pd的1，得到相应的偶联产品产量高。此外，催化剂可以重复使用而没有明显的活性损失。药物化合物和功能材料通过偶联反应合成。N 2气体吸附/解吸分析表明该催化剂具有介孔性质，在催化中起关键作用。在铃木宫浦联轴器中在聚合物基体中原位生成的钯纳米粒子具有催化活性，而聚合的Pd（II）络合物对于CH芳基化至关重要。通过XAFS，XPS，远红外吸收和拉曼光谱以及DFT计算研究了这些催化物质。
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