Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 10, Issue 48, Pages 41431-41438Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.8b16136
Keywords
metal-organic framework; nickel-catalyst; Suzuki-Miyaura cross-coupling reaction; C-C bond formation; MOF-immobilized heteroleptic catalyst
Funding
- NPRP award from the Qatar National Research Fund [NPRP9-377-1-080]
- Texas A&M University Qatar
- Qatar Foundation
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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.
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