Magnetically Separable Microporous Fe–Porphyrin Networks for Catalytic Carbene Insertion into N–H Bonds

Abstract

Microporous organic networks (MONs) are a new class of porous materials. This work shows the application of MON chemistry for the preparation of magnetically separable catalytic systems. By the Sonogashira coupling of Fe III − tetrakis(4-ethynylphenyl)porphyrin and 1,4-diiodobenzene, Fe 3 O 4 nanoparticles were coated successfully with Fe−porphyrin networks. The average thickness of the homogeneous coating was ∼17 nm. According to the powder X-ray diffraction and N 2 isotherm analyses, the Fe−porphyrin network coating exhibited amorphous and microporous characteristics. The microporous Fe−porphyrin networks on the Fe 3 O 4 nanoparticles showed good catalytic performance for carbene insertion into the N−H bond of amines. The catalytic systems were easily recycled from the reaction mixture by magnetic separation. We believe that the synthetic strategy in this work can be extended to the various catalytic systems.

Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group

“…By the Sonogashira coupling of the Fe(III) tetrakis(4-ethynylphenyl)porphyrin and 1,4-diiodobenzene, the Fe 3 O 4 nanoparticles were coated with iron(III) porphyrin networks. The resulting catalyst was easily recycled from the reaction mixture by magnetic separation, giving 100% yield for piperidine in four consecutive runs, affording only the single N-H insertion product ( Scheme 34 ) [ 93 ].…”

Gold nanoparticle modified magnetic fibrous silica microspheres as a highly efficient and recyclable catalyst for the reduction of 4-nitrophenol

“…10,11 To solve this problem, NMNPs have been grafted onto various supporting matrices to generate hybrid catalysts to protect against the aggregation of NMNPs. [19][20][21][22][23] Therefore, it is highly desirable to prepare magnetic silica materials with easy accessible high surface areas, high-efficiency mass transfer, as well as magnetic separation property, to further fabricate NMNPs-based catalysts for organic catalytic reactions. 8,[12][13][14][15][16] Although these mesoporous silicas have regular mesopores and high specific surface areas that can support NMNPs with high dispersion, their mesopores can always be easily blocked because of the small pore size.…”

Iron Coordination to Hollow Microporous Metal‐Free Disalphen Networks: Heterogeneous Iron Catalysts for CO2 Fixation to Cyclic Carbonates

“…There have been reports on the development of catalysts based on MONs . However, iron‐based MON catalysts have been relatively less explored …”

“…[10] However,i ron-basedM ON catalysts have been relatively lessexplored. [11] Our research group has studied the morphological engineering of MONs. [12] For example,b yu sing various hard templates, we have engineered hollow MON materials.…”