Recyclable and Reusable Heteroleptic Nickel Catalyst Immobilized on Metal-Organic Framework for Suzuki-Miyaura Coupling

Palani Elumalai, Hind Mamlouk, Wubulikasimu Yiming, Liang Feng, Shuai Yuan, Hong Cai Zhou, Sherzod Madrahimov

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Metal-organic frameworks (MOFs) provide highly versatile platforms to stabilize molecular catalysts that are not readily accessible under homogeneous conditions, thus enabling access to a new set of catalytic materials. Herein, we describe a recyclable and highly active nickel catalyst immobilized on MOF for Suzuki-Miyaura coupling reaction, which operates under mild conditions. This mixed ligand catalyst forms from the combination of 1 equiv of MOF-immobilized ligand, 1 equiv of nickel source, and 1 equiv of PPh3. The nature of the catalyst was verified through a series of analytical tests and catalysis experiments. The immobilized catalyst was reusable for at least up to 7 cycles without decrease in the yield of the coupled product. We also verified that this reaction does not work under homogeneous conditions and that the reaction is truly heterogeneous through "hot filtration" experiments. We identified that the reaction is first order in arylborane concentration and negative order in arylbromide concentration through the effect of substrate concentrations on the initial rate. This informed us to conduct the catalysis under slow addition of the arylbromide and reduce the catalyst loading to 1% from 3%, without detriment to the yield or rate of the reaction. The catalyst gave good to excellent isolated yields with a range of functionalities, including heterocycles on aryl bromide with widely varying electronic properties.

Original languageEnglish
Pages (from-to)41431-41438
Number of pages8
JournalACS Applied Materials and Interfaces
Volume10
Issue number48
DOIs
Publication statusPublished - 5 Dec 2018

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Keywords

  • C-C bond formation
  • metal-organic framework
  • MOF-immobilized heteroleptic catalyst
  • nickel-catalyst
  • Suzuki-Miyaura cross-coupling reaction

ASJC Scopus subject areas

  • Materials Science(all)

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