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Heteroatom Donor‐Decorated Polymer‐Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room‐Temperature Suzuki‐Miyaura Cross‐Coupling in Aqueous Media
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-08-03 , DOI: 10.1002/adsc.201800561 Simon Doherty 1 , Julian G. Knight 1 , Tom Backhouse 1 , Einas Abood 1 , Hind Al-shaikh 1 , Ashley R. Clemmet 1 , Jack R. Ellison 1 , Richard A. Bourne 2 , Thomas W. Chamberlain 2 , Rebecca Stones 2 , Nicholas J. Warren 2 , Ian J. S. Fairlamb 3 , Kevin R. J. Lovelock 4
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-08-03 , DOI: 10.1002/adsc.201800561 Simon Doherty 1 , Julian G. Knight 1 , Tom Backhouse 1 , Einas Abood 1 , Hind Al-shaikh 1 , Ashley R. Clemmet 1 , Jack R. Ellison 1 , Richard A. Bourne 2 , Thomas W. Chamberlain 2 , Rebecca Stones 2 , Nicholas J. Warren 2 , Ian J. S. Fairlamb 3 , Kevin R. J. Lovelock 4
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Palladium nanoparticles stabilized by heteroatom donor‐modified polystyrene‐based polymer immobilized ionic liquids (PdNP@HAD‐PIILP; HAD‐PPh2, OMe, NH2, CN, pyrrolidone) are highly efficient catalysts for the Suzuki‐Miyaura cross‐coupling in aqueous media under mild conditions. Catalyst modified with phosphine was consistently the most efficient as it gave high yields across a range of substrates under mild conditions at low catalyst loadings. Incorporation of polyethylene glycol into the phosphine modified immobilised ionic liquid support improved catalyst efficacy by improving dispersibility and facilitating access to the active site. Moreover, each of the heteroatom modified catalysts was more active than the corresponding unsubstituted imidazolium‐based polystyrene benchmark as well as commercial samples of Pd/C. Catalyst generated in situ from either [PdCl4]@PPh2‐PIILP or its PEGylated counterpart [PdCl4]@PPh2‐PEGPIILP, by reduction with phenylboronic acid, outperformed their pre‐formed counterparts for the vast majority of substrates examined. The turnover frequency of 16,300 h−1 obtained at room temperature is one of the highest to be reported for palladium nanoparticle‐catalysed Suzuki‐Miyaura cross‐coupling between 4‐bromoacetophenone and phenylboronic acid in aqueous media under such mild conditions.
中文翻译：
杂原子供体修饰的聚合物固定化的离子液体稳定的钯纳米颗粒：室温室温下在水性介质中铃木-宫浦交叉偶联的高效催化剂
通过杂原子供体改性的聚苯乙烯基聚合物固定的离子液体（PdNP @ HAD-PIILP； HAD-PPh 2，OMe，NH 2）稳定的钯纳米颗粒，CN，吡咯烷酮）是在温和条件下在水性介质中Suzuki-Miyaura交叉偶联的高效催化剂。用膦改性的催化剂始终是最有效的，因为它在温和条件下以低催化剂负载量提供了多种底物的高收率。将聚乙二醇掺入膦改性的固定化离子液体载体中，通过改善分散性和促进对活性位点的访问来改善催化剂的功效。此外，每种杂原子改性的催化剂都比相应的未取代的咪唑基聚苯乙烯基准以及市售的Pd / C样品更具活性。从[PdCl 4 ] @PPh 2中原位生成的催化剂‐PIILP或其聚乙二醇化的对应物[PdCl 4 ] @PPh 2 ‐PEGPIILP通过用苯基硼酸还原，在大多数受检底物上均优于其预先形成的对应物。在如此温和的条件下，室温下，钯纳米颗粒催化的Suzuki-Miyaura在4-溴苯乙酮和苯基硼酸之间的交叉偶联在室温下获得的周转频率为16,300 h -1，是报道的最高之一。
更新日期：2018-08-03
中文翻译：
杂原子供体修饰的聚合物固定化的离子液体稳定的钯纳米颗粒：室温室温下在水性介质中铃木-宫浦交叉偶联的高效催化剂
通过杂原子供体改性的聚苯乙烯基聚合物固定的离子液体（PdNP @ HAD-PIILP； HAD-PPh 2，OMe，NH 2）稳定的钯纳米颗粒，CN，吡咯烷酮）是在温和条件下在水性介质中Suzuki-Miyaura交叉偶联的高效催化剂。用膦改性的催化剂始终是最有效的，因为它在温和条件下以低催化剂负载量提供了多种底物的高收率。将聚乙二醇掺入膦改性的固定化离子液体载体中，通过改善分散性和促进对活性位点的访问来改善催化剂的功效。此外，每种杂原子改性的催化剂都比相应的未取代的咪唑基聚苯乙烯基准以及市售的Pd / C样品更具活性。从[PdCl 4 ] @PPh 2中原位生成的催化剂‐PIILP或其聚乙二醇化的对应物[PdCl 4 ] @PPh 2 ‐PEGPIILP通过用苯基硼酸还原，在大多数受检底物上均优于其预先形成的对应物。在如此温和的条件下，室温下，钯纳米颗粒催化的Suzuki-Miyaura在4-溴苯乙酮和苯基硼酸之间的交叉偶联在室温下获得的周转频率为16,300 h -1，是报道的最高之一。
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