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Preparation and application of triphenylphosphine allyl palladium halide compound and derivative thereof

A technology of triphenylphosphine and compound, which is applied in the field of catalyst synthesis, can solve the problems of poor versatility of the method, high cost of materials, cumbersome process, etc., and achieve the effects of low cost, insensitivity to oxygen and heat, and fewer steps

Active Publication Date: 2020-05-08
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] Generally speaking, the synthetic method of this type of compound of phosphine ligand allyl palladium halide that has been reported in the literature, the process is loaded down with trivial details, and material expense height, troublesome operation, method versatility is poor, so with lower cost and easy method, One-step synthesis of phosphine ligand allyl palladium halide compound and its derivatives, which is of great significance for the application and promotion of this type of complex

Method used

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  • Preparation and application of triphenylphosphine allyl palladium halide compound and derivative thereof
  • Preparation and application of triphenylphosphine allyl palladium halide compound and derivative thereof
  • Preparation and application of triphenylphosphine allyl palladium halide compound and derivative thereof

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Embodiment 1 3

[0103]Embodiment 1 Preparation of triphenylphosphine allyl palladium bromide and derivatives thereof

[0104] Step 1: Add 36mg of palladium acetate, 84mg of triphenylphosphine, 77mg of allyl bromide, 45mg of potassium tert-butoxide, and 1mL of 1,2-dichloroethane in a 50ml reaction tube, and heat to 80°C, react for 24 hours.

[0105] Step 2: After the reaction, cool to room temperature, dilute the reaction solution with dichloromethane (20 mL), filter, and dry under reduced pressure.

[0106] The third step: the crude product was stirred in petroleum ether / acetone (20:1 v / v) for 10 minutes, and filtered to obtain the product (product I) whose color and shape were yellow solids, and the yield could reach 85%. The yellow solid was recrystallized with dichloromethane / ether to obtain the structural formula [Pd(PPh 3 )(η 3 -C 3 h 5 ) Br] yellow crystal product, denoted as sample 1.

[0107] The product is carried out single crystal diffraction analysis, nuclear magnetic resona...

Embodiment 2 3

[0111] Embodiment 2 Preparation of three (p-methylphenyl) phosphine allyl palladium bromide and its derivatives

[0112] Step 1: Add 36mg of palladium acetate, 97mg of tris(p-methylphenyl)phosphine, 77mg of allyl bromide, 45mg of potassium tert-butoxide, 1mL of 1,2 dichloroethane in the reaction tube, under nitrogen atmosphere, Heated to 80°C for 24h.

[0113] Remaining steps are identical with embodiment 1. A divalent palladium yellow solid (product II) was obtained with a yield of up to 80%. The yellow solid was recrystallized from dichloromethane / ether to give the structure {Pd[P(p-Me-Ph) 3 ](η 3 -C 3 h 5 ) Br} yellow crystal product, denoted as sample 2.

[0114] The product is carried out single crystal diffraction analysis, nuclear magnetic resonance spectrum analysis and characterization, the results can be found in Figure 4 , Figure 5 and Figure 6 . Figure 4 It is a schematic diagram of the crystal structure of sample 2. It can be seen from the figure tha...

Embodiment 3 3

[0118] Example 3 Preparation of three (p-fluorophenyl) phosphine allyl palladium bromide and derivatives thereof

[0119] Step 1: Add 36mg of palladium acetate, 101mg of tris(p-fluorophenyl)phosphine, 77mg of allyl bromide, 45mg of potassium tert-butoxide, 1mL of 1,2 dichloroethane in a reaction tube, and heat under nitrogen atmosphere To 80°C, react for 24h.

[0120] Remaining steps are identical with embodiment 1. A divalent palladium yellow solid (product III) was obtained with a yield of up to 85%. The yellow solid was recrystallized from dichloromethane / ether to give the structure {Pd[P(p-F-Ph) 3 ](η 3 -C 3 h 5 ) Br} yellow crystal product, recorded as sample 3.

[0121] The product is carried out single crystal diffraction analysis, nuclear magnetic resonance spectrum analysis and characterization, the results can be found in Figure 7 , Figure 8 and Figure 9 . Figure 7 It is a schematic diagram of the crystal structure of sample 3. It can be seen from the f...

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Abstract

The invention discloses a synthesis method of a triphenylphosphine allyl palladium halide compound and a derivative thereof. The synthesis method comprises the step of carrying out one-step reaction on a mixture containing a palladium salt, a halogenated allyl compound and a trisubstituted phosphine compound to obtain the triphenylphosphine allyl palladium halide compound and the derivative thereof. The method is low in cost, high in efficiency, easy to operate and high in safety. The prepared triphenylphosphine allyl palladium halide compound and the derivative thereof can be widely applied as catalysts to catalytic cross coupling or homogeneous coupling reactions of various types of organic substrates so as to prepare various organic reaction intermediates.

Description

technical field [0001] The application relates to a preparation method of a triphenylphosphine allyl palladium halide compound and its derivatives, belonging to the field of catalyst synthesis. Background technique [0002] Palladium complexes have rich reactivity in organometallic chemistry, and they have the advantages of high efficiency, low dosage and high selectivity when used as catalysts. π-allyl palladium complexes are very important chemical reaction intermediates, which are easy to react with different nucleophilic reagents and derive rich chemical changes. Therefore, π-allyl palladium complexes are used in palladium-catalyzed organic reactions played a very important role. In addition, due to the special push-pull electronic effect of the phosphine ligand itself, it can make the change of the valence state of the central atom palladium more flexible, which is more conducive to the application of palladium complexes in the field of catalysis. [0003] Existing tr...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/24C07D209/86C07C2/36C07C15/50
CPCB01J31/2409B01J2231/4205B01J2531/824C07C2/36C07D209/86C07F15/006C07C15/50
Inventor 黄德光李影华
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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