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Heterogeneous Pd/POSS Nanocatalysts for C–C Cross‐Coupling Reactions
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-01-16 , DOI: 10.1002/slct.201702597 Vetiga Somjit 1 , Michel Wong Chi Man 2 , Armelle Ouali 2 , Preeyanuch Sangtrirutnugul 1 , Vuthichai Ervithayasuporn 1
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-01-16 , DOI: 10.1002/slct.201702597 Vetiga Somjit 1 , Michel Wong Chi Man 2 , Armelle Ouali 2 , Preeyanuch Sangtrirutnugul 1 , Vuthichai Ervithayasuporn 1
Affiliation
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An insoluble solid support of N−heterocyclic imidazolium‐functionalized cage‐like silsesquioxane (SQ); Bim‐SQ, was synthesized by nucleophilic substitution of octakis(3‐chloropropyl)octasilsesquioxane with an excess bis‐(imidazol‐1‐yl)methane and investigated as a new organic‐inorganic hybrid support. In the presence of Bim‐SQ, Pd(II) from [PdCl4]2− can be stabilized via both electrostatic interactions and imidazole‐N‐coordination, giving an amorphous material of Pd(II)@Bim‐SQ. Subsequent in situ reduction of Pd(II)@Bim‐SQ during Suzuki−Miyaura cross‐coupling reactions afforded monodispersed Pd nanoparticles (2.33 ± 1.50 nm) stablized on Bim‐SQ support, PdNp@Bim‐SQ with Pd loading up to 14% w/w. Catalytic studies revealed that the pre‐catalyst Pd(II)@Bim‐SQ was active heterogeneous catalyst for Suzuki−Miyaura cross‐coupling reactions, having the maximum TOFs of 5400 h−1 under mild conditions and in aqueous ethanol medium. Furthermore, PdNp@Bim‐SQ was also shown to be an efficient catalyst for Heck reactions. Simple catalyst recovery and reusability of PdNp@Bim‐SQ for at least 5 catalytic cycles without loss of activity were also demonstrated.
中文翻译：
用于C–C交叉偶联反应的非均相Pd / POSS纳米催化剂
N-杂环咪唑官能化的笼状倍半硅氧烷（SQ）的不溶性固体支持物；Bim-SQ是通过用过量的双（咪唑-1-基）甲烷进行亲核取代辛基（3-氯丙基）八聚倍半硅氧烷而合成的，并作为一种新的有机-无机杂化载体进行了研究。在存在Bim-SQ的情况下，[PdCl 4 ] 2−的Pd（II）可以通过静电相互作用和咪唑-N配位稳定，从而得到Pd（II）@ Bim-SQ的非晶态材料。随后的原位在Suzuki-Miyaura交叉偶联反应过程中Pd（II）@ Bim-SQ的减少提供了单分散的Pd纳米颗粒（2.33±1.50 nm），稳定在Bim-SQ载体上，PdNp @ Bim-SQ的Pd负载量高达14％w / w。催化研究表明，前催化剂Pd（II）@ Bim‐SQ是Suzuki-Miyaura交叉偶联反应的活性非均相催化剂，在温和条件下和在乙醇水溶液中的最大TOF为5400 h -1。此外，PdNp @ Bim-SQ也被证明是Heck反应的有效催化剂。还展示了PdNp @ Bim-SQ至少5个催化循环的简单催化剂回收率和可重复使用性，且没有活性损失。
更新日期：2018-01-16
中文翻译：
用于C–C交叉偶联反应的非均相Pd / POSS纳米催化剂
N-杂环咪唑官能化的笼状倍半硅氧烷（SQ）的不溶性固体支持物；Bim-SQ是通过用过量的双（咪唑-1-基）甲烷进行亲核取代辛基（3-氯丙基）八聚倍半硅氧烷而合成的，并作为一种新的有机-无机杂化载体进行了研究。在存在Bim-SQ的情况下，[PdCl 4 ] 2−的Pd（II）可以通过静电相互作用和咪唑-N配位稳定，从而得到Pd（II）@ Bim-SQ的非晶态材料。随后的原位在Suzuki-Miyaura交叉偶联反应过程中Pd（II）@ Bim-SQ的减少提供了单分散的Pd纳米颗粒（2.33±1.50 nm），稳定在Bim-SQ载体上，PdNp @ Bim-SQ的Pd负载量高达14％w / w。催化研究表明，前催化剂Pd（II）@ Bim‐SQ是Suzuki-Miyaura交叉偶联反应的活性非均相催化剂，在温和条件下和在乙醇水溶液中的最大TOF为5400 h -1。此外，PdNp @ Bim-SQ也被证明是Heck反应的有效催化剂。还展示了PdNp @ Bim-SQ至少5个催化循环的简单催化剂回收率和可重复使用性，且没有活性损失。
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