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Activity and Recyclability Improvement Through Adjusting the Tethering Strategy for Pd-Catalyzed Suzuki–Miyaura Coupling Reaction of Aryl Chlorides

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Abstract

Four mesoporous SBA-15-immobilized N-heterocyclic carbene (NHC) palladium catalysts with different nitrogen ligands were synthesized. The activity and recyclability of the catalysts were investigated in Suzuki–Miyaura cross-coupling reaction of typical aryl chlorides and arylboronic acids. Bulky NHC moiety was essential for efficiency, while tethering of nitrogen ligands on both support and NHC group could dramatically improve recyclability of the catalysts. The strategy offers an alternative strategy for designing highly efficient and recyclable immobilized catalysts.

Graphical Abstract

Mesoporous silica-immobilized palladium catalysts with the bulky N-heterocyclic carbene and tethered “throw-away”nitrogen ligands were found to be highly efficient and recyclable for Suzuki–Miyaura coupling reaction of inactive aryl chlorides.

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Acknowledgments

Financal support from the National Natural Science Foundation of China (Nos. 20871032, 20971026 and 21271047), ShanXi Science and Technology Department of China (Project No. MH2014-07), and General Administration of Quality Supervision, Inspection and Quarantine of China (Nos. 2015IK217)is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Fudan University, Shanghai, 200433, China

    Jing-Fan Zhang, Mingda Wang, Xu-Qing Guo, Hui Cao, Yuan-Long Li, Quan Zhou & Xiu-Feng Hou

  2. Technical Center for Industrial Product and Raw Material Inspection and Testing, Shanghai Entry-Exit Inspection and Quarantine Bureau, Shanghai, 200135, China

    Shu Liu

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  1. Jing-Fan Zhang
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  2. Mingda Wang
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  3. Xu-Qing Guo
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  4. Shu Liu
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  6. Yuan-Long Li
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  7. Quan Zhou
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  8. Xiu-Feng Hou
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Correspondence to Shu Liu or Xiu-Feng Hou.

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Zhang, JF., Wang, M., Guo, XQ. et al. Activity and Recyclability Improvement Through Adjusting the Tethering Strategy for Pd-Catalyzed Suzuki–Miyaura Coupling Reaction of Aryl Chlorides. Catal Lett 145, 2001–2009 (2015). https://doi.org/10.1007/s10562-015-1609-1

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  • DOI: https://doi.org/10.1007/s10562-015-1609-1

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