Pd/C-catalyzed room-temperature hydrodehalogenation of aryl halides with hydrazine hydrochloride

Cellier, Pascal P.; Spindler, Jean‐Francis; Taillefer, Marc; Cristau, Henri‐Jean

doi:10.1016/s0040-4039(03)01789-1

Cited by 107 publications

(45 citation statements)

References 15 publications

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“…37 Compared with oxidative methods, 38 reductive dehalogenation processes are advantageous in that no toxic by-products are formed. Various hydrogen donors such as metal alkoxide, 39 hydrosilanes, 40 Grignard reagents, 41 hydrazine hydrochloride, 42 and sodium formate 43 are generally available for this transformation. These reagents, however, are often harmful and toxic, and considerable amounts are required.…”

Section: Hydroxyapatitementioning

confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

142

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This account reviews a novel approach to designing high-performance heterogeneous metal catalysts using hydroxyapatites, montmorillonites, and hydrotalcites as macroligands of active metal species for aerobic alcohol oxidations, carbon-carbon bond formations, and one-pot syntheses. The catalytic systems using the above heterogeneous catalysts offer significant benefits in achieving environmentally friendly organic syntheses aiming towards Green and Sustainable Chemistry. Furthermore, the present preparation method for the immobilization of metal species is strikingly simple and allows a strong protocol for creating various nanostructured and functionalized heterogeneous catalysts.Green and Sustainable Chemistry (GSC) is a revolutionary philosophy that aims to bring about a sustainable society by improvement of the safety and environmental aspects of chemical processes and reduction of the risks of chemical products to people and the environment.1 The emphasis is on eliminating waste at the source-primary pollution prevention-rather than finding incremental end-of-pipe solutions. This concept aims to solve the societal problems of the last century associated with the mass production and consumption of materials, and plays a prime role in providing a venous function in society, encouraging reuse and circulation of resources.One of the powerful solutions in the move toward GSC is the replacement of traditional synthetic methods using harmful stoichiometric reagents that produce vast amounts of waste with cleaner and simple catalytic alternatives with high atom efficiency 1a and low E-factors. 1b Catalytic chemistry, therefore, is of ever-increasing importance because catalysis is a key element in material transformations at atomic and molecular levels, which are an essential realm of chemistry and chemical processes.Our approach to GSC is to develop a highly functionalized heterogeneous metal catalyst based on the unique characteristics of natural layered inorganic materials such as hydroxyapatite, montmorillonite, and hydrotalcite, by using them as macroligands for metal species.2 We consider the above inorganic materials to be advanced nano-scaled catalyst supports allowing for the control of the location of catalytically active metal species, which can be found, for example, on the surface, among the layers, or in the interlayer space. Furthermore, these materials are capable of creating catalytically active metal species responsible for targeted organic transformations involving monomers, chain-like species or giant clusters. The creation of well-defined active metal sites on a solid surface, as characterized by X-ray absorption spectroscopy, not only opens up an avenue to materials that boost catalytic performance, but also aids in the understanding of the molecular basis of heterogeneous catalysis. Another advantage of these catalysts is the possibility of a one-pot synthesis based on a cooperative action by several immobilized active species on the solid surface as multifunctional catalysts. The target react...

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Section: Hydroxyapatitementioning

confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

142

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“…Several compounds, such as formic acid (or formate), hydrazine and isopropanol, have been selected as hydrogen donors [3][4][5][6][7], and Pd is a commonly used catalyst. All the experiments indicated that in Pd catalyzed CTH, formic acid and hydrazine were both effective hydrogen donors, while isopropanol was less active.…”

Section: Introductionmentioning

confidence: 99%

“…Zhang et al[27] reported experimental parameters of adsorbed HCOO via ''3 bridge'' mode, the detected bond lengths of O-Pd and C-O are 2.16 ± 0.06 Å (calculated values: 2.121 Å and 2.123 Å ) and 1.26 ± 0.05 Å (calculated values: 1.274 Å and 1.274 Å ), respectively, and the O-C-O angle is 130 ± 5°( calculated values: 129.6°). Thus our calculation results are in good agreement with the previous experiment.…”

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confidence: 99%

Comparative Theoretical Study of Adsorption and Dehydrogenation of Formic Acid, Hydrazine and Isopropanol on Pd(111) Surface

2011

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Adsorption and dehydrogenation of formic acid, hydrazine and isopropanol have been investigated using periodic density functional theory (DFT). All the intermediates and transition states have been optimized and the preferred reaction pathways have been found. The adsorption energies for the most stable mode of formic acid, hydrazine and isopropanol are 38.6 kJ/mol, 63.9 kJ/mol and 46.1 kJ/mol, respectively. The dehydrogenation mechanisms of formic acid, hydrazine and isopropanol on Pd(111) surface are proposed and calculated. According to the calculation results, dehydrogenation of formate is more favorable than those of other molecules/groups, and that can be an explanation for the high reactivity of formats in Pd catalyzed transfer hydrogenation.

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“…Reduction is usually mediated by a transition-metal catalyst (Ni, Pd, Rh, Pt) and is performed with molecular hydrogen, metal hydrides or hydrogen sources such as hydrazine, formic acid and its salts, etc. [7][8][9][10][11][12][13][14][15]. For most dehalogenation reactions of aromatic halides in liquid phase, it was general to select organic solvents as the reaction medium.…”

Section: Introductionmentioning

confidence: 99%

Pd/C-catalyzed hydrodehalogenation of aromatic halides in aqueous solutions at room temperature under normal pressure

Chen

et al. 2004

Catalysis Communications

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Pd/C-catalyzed room-temperature hydrodehalogenation of aryl halides with hydrazine hydrochloride

Cited by 107 publications

References 15 publications

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Comparative Theoretical Study of Adsorption and Dehydrogenation of Formic Acid, Hydrazine and Isopropanol on Pd(111) Surface

Pd/C-catalyzed hydrodehalogenation of aromatic halides in aqueous solutions at room temperature under normal pressure

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