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Method for catalyzing cross coupling reaction of Suzuki with palladium magnesium aluminum class layered double hydroxides (LDHs)

A cross-coupling reaction, hydrotalcite technology, applied in chemical instruments and methods, preparation of organic compounds, catalyst regeneration/reactivation, etc., can solve the problems of poor palladium stability, end products and environmental pollution, and achieve high production efficiency , reduce pollution and distribute evenly

Active Publication Date: 2016-12-07
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many studies on palladium catalysts with hydrotalcite as the carrier for Suzuki cross-coupling reactions, and they are prepared by simple adsorption, impregnation, etc., which makes the stability of palladium on the carrier poor, resulting in the impact of palladium on the end products and the environment. pollution

Method used

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  • Method for catalyzing cross coupling reaction of Suzuki with palladium magnesium aluminum class layered double hydroxides (LDHs)
  • Method for catalyzing cross coupling reaction of Suzuki with palladium magnesium aluminum class layered double hydroxides (LDHs)
  • Method for catalyzing cross coupling reaction of Suzuki with palladium magnesium aluminum class layered double hydroxides (LDHs)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of catalyst PdMgAl-LDH-1 (0.50% Pd, w / w):

[0041] Weigh Mg(NO 3 ) 2 ·6H 2 O (4.590g, 17.90mmol), A1 (NO 3 ) 3 9H 2 O(2.251g, 6.00mmol), Pd(NO 3 ) 2 ·6H 2 O (0.027g, 0.10mmol), HNO 3 (0.10mol / L, 1mL) was dissolved in 12.0mL deionized water to form a mixed salt solution (A); NaOH (1.540g, 38.50mmol), NaOH 2 CO 3 (1.272g, 12.00mmol) was dissolved in 12.0mL of deionized water to prepare an alkaline solution (B). The two solutions (A) and (B) were slowly added dropwise into a three-necked round-bottomed flask filled with 9.0 mL of deionized water at the same time, vigorously stirred, and the dropping speed was controlled to maintain pH=9.5. After the dropwise addition, age in a water bath at 100°C for 13 hours, filter, wash the solid with water until neutral, and dry at 110°C for 24 hours to obtain 2.012 g of a gray solid, which is finely ground and sieved for later use.

Embodiment 2

[0043] Preparation of catalyst PdMgAl-LDH-2 (2.58% Pd, w / w):

[0044] Weigh Mg(NO 3 ) 2 ·6H 2 O (4.487g, 17.50mmol), A1 (NO 3 ) 3 9H 2 O(2.251g, 6.00mmol), Pd(NO 3 ) 2 ·6H 2 O (0.133g, 0.50mmol), HNO 3 (0.10mol / L, 1.0mL) configuration salt solution (A); NaOH (1.540g, 38.50mmol), NaOH 2 CO 3 (1.272g, 12.00mmol) Alkaline solution (B) was prepared, and the subsequent steps were the same as in Example 1 to obtain 2.012g of gray powder.

Embodiment 3

[0046] Catalyst PdMgAl-LDH-1 regeneration to prepare PdMgAl-LDH-3:

[0047] First, the deactivated catalyst PdMgAl-LDH-1 (2.000g, 0.46%Pd, w / w) was washed with hot ethanol to remove organic residues after 10 reactions (see Example 4), and then the catalyst was washed with 11.0mL 20 % nitric acid nitrate, to obtain a clear solution (A); NaOH (3.200g, 80.00mmol), Na 2 CO 3 (1.272g, 12.00mmol) Alkaline solution (B) was prepared. Subsequent steps were the same as in Example 1 to obtain 1.966 g of PdMgAl-LDH-3 catalyst, gray powder containing 0.44% Pd (w / w).

[0048] From the XRD spectrum of PdMgAl-LDH ( figure 1 ) It can be seen that around 2θ=11.6, 23.2, 34.8, 60.5 and 62.0°, there are characteristic diffraction peaks of hydrotalcite. Compared with the standard spectrum of LDHs (JCPDS 51-1525), the intensity of each diffraction peak of XRD is large, and the peak shape is sharp. Good symmetry indicates that the prepared and regenerated catalyst has good crystallinity; no other...

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Abstract

The invention discloses a method for catalyzing cross coupling reaction of Suzuki with palladium magnesium aluminum class layered double hydroxides (LDHs). The method includes that aryl halide and arylboronic acid are taken as raw materials, PdMgAl-LDHs are taken as a catalyst, and biphenyl compounds are reacted and generated under the condition that the phase transfer catalyst, alkali, additives and solvents exist. The catalyst is featured in that palladium is directly bonded on the slabs of the layered double hydroxides with even distribution and good stability. With the method, cross coupling reaction of Suzuki can be efficiently catalyzed, the catalyst is simple in preparation, easy to be regenerated and reusable, and pollution of the palladium on terminal product and environment is effectively reduced.

Description

technical field [0001] The invention belongs to the new technical field of organic synthesis, in particular to a method for palladium-magnesium-aluminum hydrotalcite catalyzing Suzuki cross-coupling reaction. Background technique [0002] Biphenyl derivatives are an important class of fine chemical intermediates, which have been widely used in the fields of drugs, dyes, organic conductors, semiconductors and liquid crystal materials ((a) Hassan, J.; Sevignon, M.; Gozzi, C. ; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470.). Palladium-catalyzed Suzuki cross-coupling reaction of various halogenated arenes and arylboronic acids is one of the important methods for the synthesis of such compounds ((a) Suzuki, A.J.Organomet.Chem.2002,653,83-90.(b) Littke, A.F.; Fu, G.C. Angew. Chem. Int. Ed. 2002, 41, 4176-4211. (c) Suzuki, A.J. Organomet. Chem. 1999, 576, 147-168.). In Suzuki cross-coupling reactions, homogeneous catalysts are usually used to improve catalytic efficien...

Claims

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Application Information

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IPC IPC(8): C07C1/32C07C15/14C07C201/12C07C205/06C07C45/68C07C49/782C07C41/30C07C43/205C07D239/26C07D213/127C07D213/16B01J23/44B01J23/96B01J38/60B01J38/64
CPCB01J23/58B01J23/96B01J38/60B01J38/64C07C1/321C07C41/30C07C45/68C07C201/12C07D213/127C07D213/16C07D239/26C07C15/14C07C205/06C07C49/782C07C43/205Y02P20/584
Inventor 郭佃顺于凯吕雪欣赵梅牟瑞琪
Owner SHANDONG NORMAL UNIV
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