NanoRu@hectorite: A heterogeneous catalyst with switchable selectivity for the hydrogenation of quinoline

Sun, Bing; Khan, Farooq-Ahmad; Vallat, Armelle; Süß‐Fink, Georg

doi:10.1016/j.apcata.2013.07.037

Cited by 37 publications

(17 citation statements)

References 38 publications

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“…The reported heterogeneous catalytic systems include catalysts based on Ru (supported on SiO 2 , hectorite, glucose‐derived carbon spheres, poly(4‐vinylpyridine), MgO, and Ru−Cu nanocages and nanocrystals), Rh (on Al 2 O 3 , ionic liquid, various metal oxides, MgO, and PEG), Pd (on hydroxyapatite, methacrylic polymer; tannin‐ and metal‐carbon stabilized), Pt (unsupported, on various metal oxides), Co (on nitrogen‐dopedgraphene), and Au (unsupported nanoporous, on TiO 2 support). The reductions have been performed with pressurized gaseous hydrogen in most cases . On the other hand, transfer hydrogenation reactions employing hydrogen donors such as PhMe 2 SiH/H 2 O, PhMe 2 SiH/EtOH, and HCOOH/triethylamine are often preferred owing to the use of simple reactors, without the need of hazardous gaseous hydrogen.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, transfer hydrogenation reactions employing hydrogen donors such as PhMe 2 SiH/H 2 O, PhMe 2 SiH/EtOH, and HCOOH/triethylamine are often preferred owing to the use of simple reactors, without the need of hazardous gaseous hydrogen. The scope of unsaturated N‐heterocycles that were reduced in the aforementioned studies comprises for instance derivatives of quinoline isoquinoline, quinoxaline, acridine, and phenanthroline …”

Section: Introductionmentioning

confidence: 99%

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Gold Particles Supported on Amino‐Functionalized Silica Catalyze Transfer Hydrogenation of N‐Heterocyclic Compounds

2016

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In this work we demonstrate that exceptionally small gold particles (d = 0.6 AE 0.2 nm) supported on amino-functionalized mesoporous silicate SBA-15 are highly active in transfer hydrogenation of structurally diverse unsaturated N-heterocyclic compounds. The heterocyclic ring is reduced selectively. The gold particles aggregate to a diameter of 4-5 nm in the presence of formic acid/triethylamine (hydrogen donor) during the first catalytic run. In subsequent cycles the nanoparticles maintain their size, yielding a very stable catalytic system that was recycled more than five times. In contrast, analogous SBA catalysts featuring larger (~5-35 nm) gold particles are not active. Excess formic acid also leads to the formation of formamide derivatives of the products of hydrogenation, which can be deformylated quantitatively. Fifteen structurally different substrates, including the scaffolds of quinoline, isoquinoline, quinoxaline, acridine, phenanthroline, quinazoline, and phenanthridine are hydrogenated and deformylated to give the amine products in > 90% overall yield. Deuterium labeling experiments indicate that 1,2-addition with subsequent disproportionation of the formed intermediate is the preferred reaction path over the 1,4addition one, suggesting the participation of a gold hydride species. . [4] However, their excellent reactivity and selectivity are accompanied by difficult or impossible catalyst separation and recycling -issues typically resolved by heterogeneous catalysis. [5] The reported heterogeneous catalytic systems include catalysts based on Ru (supported on SiO 2 , [6,7] hectorite, [8] glucose-derived carbon spheres, [9] poly(4-vinylpyridine), [10] MgO, [11] and RuÀCu nanocages and nanocrystals [12] ), Rh (on Al 2 O 3 , [13] ionic liquid, [14] various metal oxides, [15] MgO, [16] and PEG [17] ), Pd (on hydroxyapatite, [18] methacrylic polymer; [19] tannin- [20] and metal-carbon stabilized [21] ), Pt (unsupported, [22,23] on various metal oxides [15] ), Co (on nitrogendopedgraphene [24,25] ), and Au (unsupported nanoporous, [26] on TiO 2 support [27][28][29] ). The reductions have been performed with pressurized gaseous hydrogen in most cases. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]27] On the other hand, transfer hydrogenation reactions [30] employing hydrogen donors such as PhMe 2 SiH/H 2 O, [26] PhMe 2 SiH/EtOH, [29] and HCOOH/triethylamine [28] are often preferred owing to the use of simple reactors, without the need of hazardous gaseous hydrogen. The scope of unsaturated N-heterocycles that were reduced in the aforementioned studies comprises for instance derivatives of quinoline isoquinoline, [7,9,16,23,[25][26][27][28] quinoxaline, [7,9,19,25,29] acridine, [6,11,[23][24][25]27] and phenanthroline. [23] Hydrogenation catalyzed by supported gold clusters is still largely underdeveloped. The main advancement occurred around 2000, when many reports on the regioselective hydrogenation of alkenes, alkynes, aldehydes and ketones emerged. [31] However, the area of...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Gold Particles Supported on Amino‐Functionalized Silica Catalyze Transfer Hydrogenation of N‐Heterocyclic Compounds

2016

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“…Only a limited number of heterogeneous catalysts have been found active in promoting the reduction of quinolines in water under hydrogen gas. They are: Ru nanoparticles intercalated in hectorite [26], Ir complex anchored onto a solid support [27] and Pd nanoparticles stabilized by black wattle tannin [28,29], only the latter being recyclable. Recently, with the growth of green and sustainable chemistry concepts [30], considering water not only as a possible solvent [31] but also a reagent has attracted great attention in organic synthesis [32].…”

Section: Introductionmentioning

confidence: 99%

A polymer supported palladium(II) β-ketoesterate complex as active and recyclable pre-catalyst for selective reduction of quinolines in water with sodium borohydride

Dell’Anna

Romanazzi

Intini

et al. 2015

Journal of Molecular Catalysis A: Chemical

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“…37,38 Actually, some effective methods have been developed to realize selective hydrogenation by adjusting the adsorption behaviors of QL and 4H-QL. Addition of a Lewis base 39 or introduction of aprotic solvent such as n-hexane 40,41 to the reaction mixture was in favor of 10H-QL formation. Fan et al reported an excellent catalyst for complete hydrogenation of QL, Rh/AlO(OH).…”

Section: Introductionmentioning

confidence: 99%

Understanding the mechanism of the competitive adsorption in 8-methylquinoline hydrogenation over a Ru catalyst

et al. 2020

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NanoRu@hectorite: A heterogeneous catalyst with switchable selectivity for the hydrogenation of quinoline

Cited by 37 publications

References 38 publications

Gold Particles Supported on Amino‐Functionalized Silica Catalyze Transfer Hydrogenation of N‐Heterocyclic Compounds

Gold Particles Supported on Amino‐Functionalized Silica Catalyze Transfer Hydrogenation of N‐Heterocyclic Compounds

A polymer supported palladium(II) β-ketoesterate complex as active and recyclable pre-catalyst for selective reduction of quinolines in water with sodium borohydride

Understanding the mechanism of the competitive adsorption in 8-methylquinoline hydrogenation over a Ru catalyst

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