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Pyrene-4,5,9,10-quadri-imine-(arylamine) palladium chloride and application thereof in Heck reaction

A reaction and catalyst technology, applied in the field of chemistry, can solve the problems that palladium black is difficult to recycle and reuse, palladium powder is difficult to separate, etc.

Inactive Publication Date: 2015-05-13
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the homogeneous catalytic system of noble metal palladium has its own shortcomings, such as the palladium catalyst is easy to separate out the very fine palladium powder in the use process, it is difficult to separate from the system after the reaction, and the palladium black generated is difficult to recycle and reuse. Many heterogeneous palladium catalytic systems have been developed

Method used

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  • Pyrene-4,5,9,10-quadri-imine-(arylamine) palladium chloride and application thereof in Heck reaction
  • Pyrene-4,5,9,10-quadri-imine-(arylamine) palladium chloride and application thereof in Heck reaction
  • Pyrene-4,5,9,10-quadri-imine-(arylamine) palladium chloride and application thereof in Heck reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthetic method for preparing pyrene-4,5,9,10-tetraimine-(2,6-dimethylanilino)palladium(II) chloride [complex C1].

[0067]

[0068] 0.54 g (2.0 mmol) PdCl 2 (CH 3 EN) 2 Add 0.80 g (1.2 mmol) pyrene-4,5,9,10-tetraimine-(2,6-dimethylanilino) into a schlenk tube with 5 mL of dichloromethane, PdCl 2 (CH 3 EN) 2 The molar ratio to imine was 2.0:1.2, stirred at 30°C for 12 h, part of the dichloromethane was pumped out by a diaphragm pump, and 30 mL of diethyl ether was added, a reddish-brown solid precipitated, filtered through filter paper, and the filtrate was washed with diethyl ether (5 mL ×3), the washed solid was dried in a vacuum oven at 30 ℃ for 4 h to obtain 0.93 g of reddish-brown solid. Yield: 90.2%. 1 H NMR (400 MHz, CDCl 3 , ppm): 7.20 (d, J = 13.2 Hz, 4H, Ph- H ), 7.08 (d, J = 12.8 Hz, 6H, Ph- H ), 6.70-6.90 (m, 8H, Ph- H ), 2.32 (s, 6H, 2×C H 3 ), 2.18 (s, 6H, 2×C H 3 ), 1.91 (s, 6H, 2×C H 3 ), 1.32 (s, 6H, 2×C H 3 ).

[0069] 13 C...

Embodiment 2

[0071] Synthetic method for preparing pyrene-4,5,9,10-tetraimine-(2,6-diethylanilino)palladium(II) chloride [complex C2].

[0072]

[0073] 0.54 g (2.0 mmol) PdCl 2 (CH 3 EN)2 Add to 0.93 g (1.2 mmol) pyrene-4,5,9,10-tetraimine-(2,6-diethylanilino) into a schlenk tube with 5 mL of dichloromethane, PdCl 2 (CH 3 EN) 2 The molar ratio to imine was 2.0:1.2, stirred at 30°C for 12 h, part of the dichloromethane was pumped out by a diaphragm pump, and 30 mL of diethyl ether was added, a reddish-brown solid precipitated, filtered through filter paper, and the filtrate was washed with diethyl ether (5 mL ×3), the washed solid was dried in a vacuum oven at 30 ℃ for 4 h to obtain 0.68 g of reddish-brown solid. Yield: 59.6%.

Embodiment 3

[0075] Synthetic method for preparing pyrene-4,5,9,10-tetraimine-(2,4,6-trimethylanilino)palladium(II) chloride [complex C3].

[0076]

[0077] 0.54 g (2.0 mmol) PdCl 2 (CH 3 EN) 2 Add 0.87 g (1.2 mmol) pyrene-4,5,9,10-tetraimine-(2,4,6-trimethylanilino) to a schlenk tube with 5 mL of dichloromethane, PdCl 2 (CH 3 EN) 2 The molar ratio to imine was 2.0:1.2, stirred at 30°C for 12 h, part of the dichloromethane was pumped out by a diaphragm pump, and 30 mL of diethyl ether was added, a reddish-brown solid precipitated, filtered through filter paper, and the filtrate was washed with diethyl ether (5 mL ×3), the washed solid was dried in a vacuum oven at 30 °C for 4 h to obtain 0.90 g of reddish-brown solid. Yield: 83.3%.

[0078] 1 H NMR (400 MHz, CDCl 3 , ppm): 7.05 (s, 4H, Ph- H ), 6.97-7.01 (m, 4H, Ph- H ), 6.76-6.80 (m, 3H, Ph- H ), 6.53-6.69 (m, 3H, Ph- H ), 2.38 (s, 6H, 2×C H 3 ), 2.19-2.37 (m, 24H, 8×C H 3 ), 1.30 (s, 6H, 2×C H 3 ). 13 C NMR (100 MHz...

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Abstract

The invention provides a Pd complex catalyst as well as a preparation method and application thereof. The structural formula of the Pd metal complex catalyst provided by the invention is shown in the formula II (shown in the description), wherein R1 and R are H and alkyl groups; preferably, R is a methyl or ethyl, and R1 is H or the methyl. According to the invention, a small amount of the Pd metal complex catalyst can be used to promote the Heck reaction, has an excellent catalytic performance and can catalyze the Heck reaction, and the formula I is also shown in the description.

Description

technical field [0001] The invention belongs to the field of chemistry, in particular to a Pd complex catalyst and its application in heck reaction. Background technique [0002] The Heck reaction was developed by Mizoroki [T. Mizoroki, K. Mori, A. Ozaki, Arylation of Olefin with Aryl Iodide Catalyzed by Palladium, Bull. Chem. Soc. Jap. 1971, 44 , 581.] and Heck [R. F. Heck, J. P. Nolley. Jr, Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides, J. Org. Chem. 1972, 37 , 2320.] et al. discovered in 1971 and 1972 respectively, this type of reaction is an important means to form new C—C connected by unsaturated double bonds, and has gradually developed into an increasingly applied Extensive methods of organic synthesis. Heck himself also won the 2010 Nobel Prize in Chemistry for his outstanding contribution in this area. But the homogeneous catalytic system of noble metal palladium has its own shortcomings, such as the palladium c...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07F15/00C07B37/04C07C15/46C07C1/32C07C39/21C07C37/18C07C211/45C07C209/68C07C43/215C07C41/30C07D213/16C07D213/127
Inventor 赵同班青
Owner QILU UNIV OF TECH
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