Development of recyclable iridium catalyst for C–H borylation

Tagata, Tsuyoshi; Nishida, Motohiro; Nishida, Atsushi

doi:10.1016/j.tetlet.2009.08.080

Cited by 23 publications

(7 citation statements)

References 25 publications

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“…In homogeneous catalysis, the Ir-bipyridine complex was found to show both high catalytic activity and functional tolerance for direct C–H borylation of arenes, one of the most important transformations for preparing useful aryl boryl ester intermediates . To date, heterogeneous molecular catalysts for C–H borylation have been limited to the Ir-silica-supported phosphine complex and polymeric Ir-bipyridine complex catalysts . Herein, BPy-PMO was used as a solid chelating ligand for the heterogeneous Ir-catalyst for direct C–H borylation of arenes.…”

Section: Resultsmentioning

confidence: 99%

A Solid Chelating Ligand: Periodic Mesoporous Organosilica Containing 2,2′-Bipyridine within the Pore Walls

Maegawa²,

et al. 2014

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Synthesis of a solid chelating ligand for the formation of efficient heterogeneous catalysts is highly desired in the fields of organic transformation and solar energy conversion. Here, we report the surfactant-directed self-assembly of a novel periodic mesoporous organosilica (PMO) containing 2,2'-bipyridine (bpy) ligands within the framework (BPy-PMO) from a newly synthesized organosilane precursor [(i-PrO)3Si-C10H6N2-Si(Oi-Pr)3] without addition of any other silane precursors. BPy-PMO had a unique pore-wall structure in which bipyridine groups were densely and regularly packed and exposed on the surface. The high coordination ability to metals was also preserved. Various bipyridine-based metal complexes were prepared using BPy-PMO as a solid chelating ligand such as Ru(bpy)2(BPy-PMO), Ir(ppy)2(BPy-PMO) (ppy = 2-phenylpyridine), Ir(cod)(OMe)(BPy-PMO) (cod = 1,5-cyclooctadiene), Re(CO)3Cl(BPy-PMO), and Pd(OAc)2(BPy-PMO). BPy-PMO showed excellent ligand properties for heterogeneous Ir-catalyzed direct C-H borylation of arenes, resulting in superior activity, durability, and recyclability to the homogeneous analogous Ir catalyst. An efficient photocatalytic hydrogen evolution system was also constructed by integration of a Ru-complex as a photosensitizer and platinum as a catalyst on the pore surface of BPy-PMO without any electron relay molecules. These results demonstrate the great potential of BPy-PMO as a solid chelating ligand and a useful integration platform for construction of efficient molecular-based heterogeneous catalysis systems.

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Section: Resultsmentioning

confidence: 99%

A Solid Chelating Ligand: Periodic Mesoporous Organosilica Containing 2,2′-Bipyridine within the Pore Walls

Maegawa²,

et al. 2014

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“…Recently, we reported the preparation of a recyclable iridium catalyst for the CH borylation reaction 11. The iridium catalyst, which can be prepared from an iridium precursor, 2,2′‐bipyridine‐4,4′‐dicarboxylic acid (BPDCA) and bis(pinacolato)diboron (Pin 2 B 2 , 1 ), could be reused at least ten times in the borylation of benzene.…”

Section: Methodsmentioning

confidence: 99%

“…First, we synthesized a recyclable iridium catalyst according to our procedure (Scheme ) 11. A mixture of iridium precursor [IrCl(COD)] 2 (1.2 mmol) with 2,2′‐bipyridine‐4,4′‐dicarboxylic acid (2.4 mmol) in benzene (21.4 mL, 240 mmol) was heated at 80 °C for 4 h in the presence of Pin 2 B 2 1 (8.0 mmol).…”

Section: Methodsmentioning

confidence: 99%

Controlled Synthesis of Nanoscale Icosahedral Gold Particles at Room Temperature

et al. 2012

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The shape of nanocrystals determines surface atomic arrangement and coordination, influencing their chemical and physical properties. We present a novel and facile approach to synthesize gold icosahedra by employing glucose as reducing reagent and sodium dodecyl sulfate as directing agent in the environmentally benign medium of water at room temperature. The size of the icosahedra can be controlled in the range of 30–250 nm by altering reaction conditions. High‐resolution microscopy and diffraction studies indicate the icosahedra are composed of rotational twins that owe likely to assemblage of tetrahedral units. The gold icosahedra particles catalytic properties are probed in the borohydride reduction of p‐nitrophenols and exhibit a size‐dependence reaction property. Comparison studies with spherical particles prepared by the Turkevich method, coupled with poisoning experiments, infer that the shape has a strong influence in the abundance of active surface sites as well as their activities. The properties of nanoscale icosahedra particles has promising applications for further catalytic processes, surface enhancement spectroscopic methods, chemical or biological sensing, and the fabrication of nanoscale devices.

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“…Recently, molecular heterogeneous catalysts have attracted significant research interest for C–H activation using various solids as supports, such as polymer, 18 metal–organic frameworks (MOFs), 19 and silica-based materials. 11 , 20 – 22 For example, Lin et al synthesized UiO-type MOFs with 2,2′-bipyridine (bpy) as an orthogonal functional fragment to form solid catalysts for both borylation of C–H bonds and ortho -silylation of benzylic silyl ethers.…”

Section: Introductionmentioning

confidence: 99%

Molecular heterogeneous catalysts derived from bipyridine-based organosilica nanotubes for C–H bond activation

Zhang

Wang

et al. 2017

Chem. Sci.

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Development of recyclable iridium catalyst for C–H borylation

Cited by 23 publications

References 25 publications

A Solid Chelating Ligand: Periodic Mesoporous Organosilica Containing 2,2′-Bipyridine within the Pore Walls

A Solid Chelating Ligand: Periodic Mesoporous Organosilica Containing 2,2′-Bipyridine within the Pore Walls

Controlled Synthesis of Nanoscale Icosahedral Gold Particles at Room Temperature

Molecular heterogeneous catalysts derived from bipyridine-based organosilica nanotubes for C–H bond activation

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