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Self-loading diphosphine-palladium catalyst and preparation method and application thereof

A self-supporting bisphosphine and palladium catalyst technology, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of metal catalyst product pollution, low catalytic activity, etc., and achieve excellent catalytic effect, high heat Stability, simple and feasible reaction route

Active Publication Date: 2017-08-25
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generally, the coupling reaction can be efficiently carried out in the presence of homogeneous palladium catalysts, however, there are still some disadvantages in homogeneous palladium catalysis, including separation, recovery and reuse of catalysts, and product contamination caused by incomplete separation of metal catalysts. question
A typical approach to solve these problems is to anchor palladium catalysts on suitable supports to make corresponding heterogeneous palladium catalysts, however some of these heterogeneous palladium catalysts show lower catalytic activity compared with their homogeneous counterparts , so further progress is still needed on the enhancement of the activity of heterogeneous palladium catalysts

Method used

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  • Self-loading diphosphine-palladium catalyst and preparation method and application thereof
  • Self-loading diphosphine-palladium catalyst and preparation method and application thereof
  • Self-loading diphosphine-palladium catalyst and preparation method and application thereof

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Embodiment 1-8

[0028] Embodiment 1-8: the preparation method of bisphosphine-palladium catalyst.

[0029]

Embodiment 1

[0031] Magnesium chips (144 mg, 6 mmol), 1 capsule (about 35 mg, the same below) iodine and 1,4-dibromobenzene (468 mg, 2 mmol) dissolved in dry N,N'-dimethylformaldehyde Amide (6 mL), reacted at 40 °C for 6 h, added diphenylphosphorous chloride (880 mg, 4 mmol), stirred at room temperature for 8 h, washed with ammonium chloride aqueous solution after the reaction, extracted with ethyl acetate, dried, and passed through the column Chromatography (petroleum ether as developer) gave 1 (268 mg, 60%) as a white solid. M.p. 166-167 °C; IR (KBr): υ 3053, 1478, 1433, 1092, 821, 741, 694, 552, 513, 483 cm -1 ; 1 H-NMR (600 MHz, CDCl 3 , 25 ℃, TMS): δ = 7.22-7.24 (m, 4H), 7.31-7.33 (m, 20H); 13 C-NMR (150 MHz, CDCl 3 , 25℃, TMS): δ = 128.49, 128.82, 133.34, 133.80, 136.71, 137.93; 31P-NMR (240MHz,CDCl 3 , 25 ℃, TMS): δ = -6.64.

Embodiment 2

[0033] Dissolve magnesium chips (288 mg, 12 mmol), 1 grain of iodine and 1,4-dibromobenzene (624 mg, 2 mmol) in dry tetrahydrofuran (6 mL), react at 60 °C for 8 h, add diphenylphosphine Chlorine (880 mg, 4 mmol), stirred at room temperature for 8 h, washed with ammonium chloride aqueous solution after the reaction, extracted with ethyl acetate, dried, and obtained white solid 1 (335 mg, 75 %). M.p. 166-167 °C; IR (KBr): υ 3053, 1478, 1433, 1092, 821, 741, 694, 552,513, 483 cm -1 ; 1 H-NMR (600 MHz, CDCl 3 , 25 ℃, TMS): δ = 7.22-7.24 (m, 4 H),7.31-7.33 (m, 20 H); 13 C-NMR (150 MHz, CDCl 3 , 25 ℃, TMS): δ= 128.49, 128.82, 133.34, 133.80, 136.71, 137.93; 31 P-NMR (240 MHz, CDCl 3 , 25 ℃, TMS): δ=-6.64.

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Abstract

The invention relates to a self-loading diphosphine-palladium catalyst and a preparation method and application thereof. According to the preparation method, diphenyl phosphorous chloride is used as a raw material, and after the chloride is replaced by a Grignard reagent, the raw material is coordinated with palladium bichloride to form the catalyst. The catalyst has the advantages that (1), the catalyst has higher thermal stability; (2), the catalyst can be used for catalyzing a Suzuki-Miyaura coupling reaction under a mild condition and acquires an excellent catalyzing effect; (3), after a catalyzing reaction is completed, the catalyst can be reused through simple centrifugal filtration, and the difficult problem of recycling and reutilization of a homogeneous catalyst is solved. The preparation method is simple and feasible in reaction routes, and the catalyst can be used as an efficient catalyst to be applied to the synthesis of medicines, spices, pesticides and functional materials.

Description

technical field [0001] The invention relates to a self-supporting bisphosphine-palladium catalyst as well as its preparation method and application. Background technique [0002] Palladium-catalyzed Suzuki-Miyaura coupling reactions of aryl halides with arylboronic acids are the most efficient synthetic transformation pathways for the construction of fine chemicals, pharmaceuticals, and agrochemicals. Generally, the coupling reaction can be efficiently carried out in the presence of homogeneous palladium catalysts, however, there are still some disadvantages in homogeneous palladium catalysis, including separation, recovery and reuse of catalysts, and product contamination caused by incomplete separation of metal catalysts. question. A typical approach to solve these problems is to anchor palladium catalysts on suitable supports to make corresponding heterogeneous palladium catalysts, however some of these heterogeneous palladium catalysts show lower catalytic activity comp...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/24C07C1/32C07C15/14C07C41/30C07C43/205C07C45/68C07C49/784
CPCC07C1/321C07C41/30C07C45/68C07F15/0066B01J31/2409C07C15/14C07C43/205C07C49/784
Inventor 聂俊琦卢翠芬王亦鸣杨桂春陈祖兴王飞翼
Owner HUBEI UNIV
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