Immobilization of NHC-Bearing Palladium Catalysts on Polyvinylpyridine; Applications in Suzuki-Miyaura and Hartwig-Buchwald Reactions under Batch and Continuous-Flow Conditions

被引:35
|
作者
Mennecke, Klaas [1 ]
Kirschning, Andreas [1 ]
机构
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
来源
SYNTHESIS-STUTTGART | 2008年 / 20期
关键词
microreactor; heterogeneous catalysis; Hartwig-Buchwald reaction; palladium; Suzuki-Miyaura reaction; immobilization;
D O I
10.1055/s-2008-1067274
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The facile coordinative immobilization of Organ's PEPPSI (TM) catalyst on a composite material composed of megaporous glass and polyvinylpyridine is described. The catalyst showed very good performance in Suzuki-Miyaura as well as Hartwig-Buchwald reactions of aryl chlorides under mild conditions and with low catalyst loadings. The modified PEPPSI (TM) catalyst was probed both under batch mode and continuous-flow applications. The flow setup was also utilized to shed light on the stability of the PEPPSI (TM) catalyst and the mobility of palladium.
引用
收藏
页码:3267 / 3272
页数:6
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    Huskens, Jurriaan
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    Loponov, Konstantin
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    Khan, J
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  • [9] The first use of porphyrins as catalysts in cross-coupling reactions: a water-soluble palladium complex with a porphyrin ligand as an efficient catalyst precursor for the Suzuki-Miyaura reaction in aqueous media under aerobic conditions
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    Coutsolelos, Athanassios G.
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    Ley, SV
    McConvey, IF
    Al-Duri, B
    Leeke, GA
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