A new generation of homogeneous arene hydrogenation catalysts

Rothwell, Ian P.

doi:10.1039/a606985a

Cited by 119 publications

(77 citation statements)

References 53 publications

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“…Table 26). It was found that Nb and Ta alkoxide complexes are also able to hydrogenate unfunctionalized aromatic rings [82] (Table 26), but the catalysts proved to be very sensitive and the functional group tolerance was low. Colloidal Ru [61a] and Rh [61bÀd] catalysts were shown to be active for the hydrogenation of various aromatic systems, in part under very mild conditions (see Table 26).…”

Section: Novel Catalystsmentioning

confidence: 98%

Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments

Blaser¹,

Malan²,

Pugin³

et al. 2003

Adv Synth Catal

1,290

493

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In this overview, recent trends and developments for the selective hydrogenation of multifunctional molecules are discussed and assessed from the point of view of fine chemicals synthesis. In a first part, the design and preparation of catalysts and ligands with interesting properties are summarized, particularly meant for the catalysis specialist. The following topics are described in some detail: How enantioselective homogeneous catalysts are designed and tested; new effective chiral monodentate phosphines; successful bidentate phosphines ligand families (with axially chiral biaryl-and ferrocenyl-based backbones, new phospholanes and with stereogenic phosphorus); novel bidentate ligand families with P-O and P-N bonds; and oxazoline-based ligands. A short overview on immobilized chiral complexes and of the toolbox of heterogeneous catalysis (bimetallic, colloidal and modified catalysts) concludes this chapter. In a second part, progress for selected catalytic transformations and generic selectivity problems is described, intended mainly for the organic chemist who has to solve specific synthetic problems. Emphasis is on the following topics: The enantioselective hydrogenation of olefins with various substitution patterns; the chemo-and enantioselective hydrogenation of ketones; the diastereo-and enantioselective hydrogenation of C N functions; the stereoselective hydrogenation of aromatic rings; chemoselectivity and hydroxylamine accumulation in the reduction of functionalized nitroarenes; chemoselectivity and new protecting groups for catalytic debenzylation; the mild hydrogenation of carboxylic acid derivatives; and the chemoselective hydrogenation of nitriles. In the last parts of the review, transfer hydrogenation and mechanistic issues are discussed, followed by a short conclusions and outlook paragraph.

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Section: Novel Catalystsmentioning

confidence: 98%

Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments

Blaser¹,

Malan²,

Pugin³

et al. 2003

Adv Synth Catal

1,290

493

View full text Add to dashboard Cite

show abstract

“…Similarly, the relative rate of anthracene (C 14 H 10 ) hydrogenation to tetrahydroanthracene (C 14 H 14 ) was 21 and subsequent hydrogenation to octahydroanthracene was determined to be 3. Hydrogenation of phenanthrene (C 14 H 10 ) to sym-tetrahydrophenanthrene (C 14 H 14 ) was 1.3 or to asymmetric tetrahydrophenanthrene was 0.7 [9].…”

Section: Hydrogenations Of Fused Ringsmentioning

confidence: 99%

Catalytic hydrogenation of polycyclic aromatic hydrocarbons over palladium/γ-Al2O3 under mild conditions

Yuan

Marshall

2005

Journal of Hazardous Materials

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“…[3] Rothwell et al have used homogenous niobium and tantalum catalysts for the hydrogenation of arenes and arylphosphines. [4] Finke et al reported that metal nanoparticles act as catalysts for the hydrogenation of arenes and ketones. [5] As recyclable catalysts, molecular rhodium catalysts tethered to a palladium-silica support [6] or ionic copolymer [7] have been reported.…”

Section: Introductionmentioning

confidence: 99%

Rhodium and Iridium Nanoparticles Entrapped in Aluminum Oxyhydroxide Nanofibers: Catalysts for Hydrogenations of Arenes and Ketones at Room Temperature with Hydrogen Balloon

et al. 2007

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Abstract:The recyclable metal nanoparticle catalysts, rhodium in aluminum oxyhydroxide [Rh/ AlO(OH)] and iridium in aluminum oxyhydroxide [Ir/AlO(OH)], were simply prepared from readily available reagents. The catalysts showed high activities in the hydrogenation of various arenes and ketones under mild conditions. Selective hydrogenation was possible for bicyclic and tricyclic arenes in high yields. The catalysts were active at room temperature even with a hydrogen balloon. Also, the catalysts showed high turnover frequency (TOF) values under solventless conditions at 75 8C under 4 atm hydrogen pressure: ca. 1700 h À1 in the hydrogenation of benzene. Furthermore, Rh/AlO(OH) can be reused for at least 10 times without activity loss. The catalysts were characterized by the transmission electron microscopy (TEM), powder X-ray diffraction (XRD), inductively coupled plasma (ICP), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), nitrogen adsorption and hydrogen chemisorption experiments. The sizes of rhodium and iridium particles were estimated to be 3-4 nm and 2-3 nm, respectively. Aluminum oxyhydroxide nanofibers of these catalysts have surface areas of 500-600 m 2 g À1 .

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A new generation of homogeneous arene hydrogenation catalysts

Cited by 119 publications

References 53 publications

Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments

Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments

Catalytic hydrogenation of polycyclic aromatic hydrocarbons over palladium/γ-Al2O3 under mild conditions

Rhodium and Iridium Nanoparticles Entrapped in Aluminum Oxyhydroxide Nanofibers: Catalysts for Hydrogenations of Arenes and Ketones at Room Temperature with Hydrogen Balloon

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