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Process for the production of palladium supported catalysts for catalyzing heck, suzuki-miyaura sonogashira coupling and buchwald-hartwig reactions

A technology for chemical reactions and heterogeneous catalysts, applied in catalytic reactions, carbon compound catalysts, chemical instruments and methods, etc., can solve the problems of low yield, insufficient stability of coordination compounds and high leakage

Inactive Publication Date: 2010-03-24
NORDIC CHEMQUEST AB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalyst was not as efficient as expected for heterogeneous C-C and C-N couplings and only small yields were observed
[0005] However, it is also clear that the complex is not stable enough and there is an unacceptably and uncontrollably high leaching of highly active and inactive palladium from the beads

Method used

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  • Process for the production of palladium supported catalysts for catalyzing heck, suzuki-miyaura sonogashira coupling and buchwald-hartwig reactions
  • Process for the production of palladium supported catalysts for catalyzing heck, suzuki-miyaura sonogashira coupling and buchwald-hartwig reactions
  • Process for the production of palladium supported catalysts for catalyzing heck, suzuki-miyaura sonogashira coupling and buchwald-hartwig reactions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: catalyst preparation

[0045] Will IRA 900 (chloride form) (Acros, BE) was packed into a column and treated repeatedly with 0.5% sodium formate solution until a negative response to chloride ions was observed. The resin was then washed with water until it exhibited a low conductivity response and dried under vacuum. Palladium acetate (20 mg, 0.089 mmol) was added to a suspension of ARF (2 g) in DMF (4 ml), and the 2 The mixture was stirred at room temperature for 1 hour and then at 50°C for 3 hours. Orange or dark orange solutions become completely colorless, while ARF beads turn black. In a control experiment, using IRA 900 (chloride form) and Pd(OAc) 2 or Na 2 PdCl 4 This color change was not observed, suggesting that in the presence of counterions (formate as a reducing source), Pd (II) is reduced to Pd (0) and is adsorbed on the resin surface. At this point, the gray beads turned black and the dark orange supernatant became completely col...

Embodiment 2

[0046] Example 2: From Na 2 PdCl 4 Start to prepare the catalyst

[0047] Repeat the method of embodiment 1, just use the Na of equimolar amount 2 PdCl 4 Replacement of Pd(OAc) 2 . get similar results.

[0048] Will IRA 900 (chloride form) (Acros, BE) was packed into a column and treated repeatedly with 0.5% sodium formate solution until a negative response to chloride ions was observed. The resin was then washed with water until it exhibited a low conductivity response and dried under vacuum. Then, the dried resin (2 g) was placed in methanol and allowed to stand for 2 hours. Excess methanol was removed and palladium acetate (20 mg, 0.089 mmol) diluted in DMF (15 ml) was added under N 2 The mixture was stirred at room temperature for 1 hour and then at 50°C for 3 hours. Orange or dark orange solutions become completely colorless, while ARF beads turn black. In a control experiment, using IRA 900 (chloride form) and Pd(OAc) 2 or Na 2 PdCl 4 This color ch...

Embodiment 3

[0050] Example 3: FT-IR Spectrum of New Pd Catalyst

[0051] The new Pd catalyst was first characterized by IR spectroscopy. Carboxylate consists of two identical The bond is precisely represented by the resonance-stabilized carboxylate anion, thus giving antisymmetric and symmetric stretch absorption. In Table 1 the FT-IR spectral data for different formate, ARF and new Pd catalysts are given. The new Pd catalyst and ammonium formate (HCOONH 4 ), potassium formate (HCOOK) and ARF for comparison. 1595-1593cm observed -1 range due to HCOONH 4 , HCOOK, and ARF's carboxylate anions caused by antisymmetric stretching, while the new Pd catalyst absorbs at 1653 cm -1 . Similar observations were noted in the case of symmetric stretching of carboxylate anions. v of the new Pd catalyst max A significant increase in α indicates possible palladium metal deposition and possible bonding of palladium metal to the formate carbonyl.

[0052] Table 1: Carboxylate anion FT-IR data ...

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Abstract

A method of producing a heterogeneous catalyst suitable for catalyzing Heck, Suzuki-Miyaura and Buchwald-Hartwig reactions, comprising the steps of: a) providing a porous carrier, said porous carrierconsisting of a core and a plurality of ion exchange groups covalently bonded to the surface of said core, where at least 90 % of the ions bound to said carrier are formate ions; b) providing a palladium (II) salt; c) suspending said carrier in an organic solvent thereby obtaining a suspension; d) adding said palladium salt to said suspension and allowing the resulting mixture to react at a temperature within the range of 30 - 70 DEG C until said carrier has turned black; e) washing said carrier in water; and f) drying said carrier under vacuum; characterised in that the resulting carrier subsequently is resuspended in dimethyl formamide and heated under inert atmosphere to at least 90 DEG C for 2 hours followed by washing with a polar solvent and drying. The invention also relates to acatalyst produced by the method and to processes where the catalyst is used for catalysing Heck, Suzuki-Miyaura, and Buchwald-Hartwig reactions.

Description

[0001] The present invention relates to novel catalysts suitable for catalyzing Heck, Suzuki-Miyaura, Sonogashira couplings and Buchwald-Hartwig reactions. The present invention also provides methods and processes for producing catalysts for use in catalyzing Heck, Suzuki-Miyaura, Sonogashira coupling and Buchwald-Hartwig reactions. Background technique [0002] Transition metal-catalyzed organic reactions form a central part of contemporary organic synthesis. In particular, palladium-catalyzed carbon-carbon and carbon-heteroatom (N and O) bonding processes represent the most important reactions in the field of organic process development. All documents cited in this specification are hereby incorporated by reference unless otherwise indicated. While the Heck, Sonogashira coupling and Suzuki-Miyaura reactions are excellent tools for carbon-carbon coupling reactions between aryl halides or trifluorides and suitable counterparts, Buchwald-Hartwig developed a method for carbon ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J23/44B01J31/08B01J37/06C07C37/18C07C39/15C07C41/30C07C69/612C07C69/618C07D213/61C07D401/04C07D413/04C07D491/147
CPCB01J31/165C07C37/18C07C67/343C07C41/30C07C17/263C07D213/61B01J2231/4211B01J37/06C07C2103/24C07C2531/08C07D413/04B01J2531/824B01J2231/4261C07C2523/44C07C1/321C07D491/147B01J31/08C07D401/04B01J23/44C07C2603/24C07C15/14C07C25/18C07C69/618C07C69/65C07C43/205C07C39/15
Inventor 弗雷德里克·阿尔姆奎斯特巴苏德布·巴苏
Owner NORDIC CHEMQUEST AB
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