Highly Efficient Heterogeneous Aqueous Kharasch Reaction with an Amphiphilic Resin‐Supported Ruthenium Catalyst

Oe, Yohei; Uozumi, Yasuhiro

doi:10.1002/adsc.200800359

Cited by 41 publications

(23 citation statements)

References 35 publications

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“…Catalyst recycling is another important issue in ATRA systems. The design of solid supported catalysts [11] ( Figure 1) and also their use in aqueous media [12] have contributed to eliminate the tedious and environmental unfriendly catalyst separation steps. Clark and co-workers have described a range of silica, polystyrene, or JandaJel resin supported copper catalysts bearing pyridinemethanimine or polyamine ligands for ATRC reactions (Figure 1 c).…”

Section: Introductionmentioning

confidence: 99%

Atom Transfer Radical Reactions as a Tool for Olefin Functionalization – On the Way to Practical Applications

2011

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Transition‐metal‐catalyzed atom transfer radical reactions of halogenated compounds with olefins constitute a versatile tool in organic synthesis within the area of C–C bond forming transformations. The inter‐ or intramolecular versions, atom transfer radical addition (ATRA) or cyclization (ATRC), respectively, lead to the atom‐economic, useful synthesis of compounds that can be further functionalized. This contribution summarizes the recent developments in this area in terms of catalyst design as well as the applicability of this methodology in sequential, domino, or tandem reactions.

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Section: Introductionmentioning

confidence: 99%

Atom Transfer Radical Reactions as a Tool for Olefin Functionalization – On the Way to Practical Applications

2011

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“…Over the past five years, catalyst regeneration in ATRA has attracted considerable academic interest (Blackman, 2008;Díaz-Álvarez et al, 2008;Eckenhoff & Pintauer, 2010a;Iizuka et al, 2007;Lundgren et al, 2008;Maiti et al, 2008;Oe & Uozumi, 2008;Pintauer, 2010;Thommes et al, 2007;Wallentin et al, 2012;Wolf et al, 2008) and was successfully applied to intramolecular ATRA or atom transfer radical cyclization (ATRC) and sequential ATRA followed by [3+2] azide-alkyne cycloaddition reactions (Clark & Wilson, 2008;Muñoz-Molina et al, 2008;Nguyen et al, 2011;Sebren et al, 2014;Thommes et al, 2007;Wolf et al, 2008).…”

Section: Towards Diminishing Concentrations Of Copper Catalysts In Atmentioning

confidence: 99%

Towards the development of highly active copper catalysts for atom transfer radical addition (ATRA) and polymerization (ATRP)‡

Pintauer

2016

Chemical Papers

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Fundamentals of copper catalyzed atom transfer radical addition (ATRA) and mechanistically similar polymerization (ATRP) were discussed. Special emphasis was placed on structural characterization and electrochemical properties of copper complexes. Recent advances in the development of highly active copper complexes for both processes were also reviewed. It was found that electrondonating groups (methoxy and methyl in the 4 and 3,5 positions, respectively) of the pyridine rings in tris(2-pyridylmethyl)amine (TPMA) ligand, significantly increase the catalytic activity in copper mediated ATRA/ATRP.

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“…The polymers serve in most cases as a solubilizer for the catalyst in different solvents, from organic solvents to aqueous media, and can be recycled by precipitation in appropriate solvents. To improve catalyst recycling, polymer resins such as the Merrifield resin have been successfully used and for more polar solvents, such as water or dimethylformamide, the PEG‐ylated variant which is also known as TentaGel® has been utilized …”

Section: Introductionmentioning

confidence: 99%

Bipyridine copper functionalized polymer resins as support materials for the aerobic oxidation of alcohols

Sand

Weberskirch

2016

Polymer International

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Here, we report the first polymer resin supported Cu(I)/bipyridine/N-oxyl catalyst systems for the aerobic oxidation of alcohols at room temperature with ambient air. We chose polystyrene-poly(ethylene glycol) copolymer (TentaGel ® ) and Merrifield resin as support materials because of their different swelling properties in polar and nonpolar solvents. The bromo functionalized TentaGel resin TG1 or Merrifield resin MR1 were functionalized with 4,4 ′ -dimethoxy-2,2 ′ -bipyridine ( MeO bpy) to give the ligand modified polymer resin TG2/MR2 that was loaded with Cu I (Br) to give the final Cu I (Br)/bipyridine support TG3/MR3. These resins were characterized by Fourier transform infrared, SEM, SEM energy dispersive X-ray spectroscopy and elemental analysis. Catalytic activity and recyclability of TG3 was investigated in acetonitrile and cyclohexane and displayed high activities in acetonitrile but also high metal leaching. In cyclohexane as solvent leaching was reduced to 1% − 2%, and catalytic activity was still at 75% after the fifth run. MR3 was consequently tested in cyclohexane and toluene. In both solvents low metal leaching was observed with higher activity in toluene as solvent, showing still over 90% conversion after the seventh run with 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO) and 80% with 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO).

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Highly Efficient Heterogeneous Aqueous Kharasch Reaction with an Amphiphilic Resin‐Supported Ruthenium Catalyst

Cited by 41 publications

References 35 publications

Atom Transfer Radical Reactions as a Tool for Olefin Functionalization – On the Way to Practical Applications

Atom Transfer Radical Reactions as a Tool for Olefin Functionalization – On the Way to Practical Applications

Towards the development of highly active copper catalysts for atom transfer radical addition (ATRA) and polymerization (ATRP)‡

Bipyridine copper functionalized polymer resins as support materials for the aerobic oxidation of alcohols

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