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Novel chiral polydentate ligand, metal-organic coordination polymer formed through coordination, and application of metal-organic coordination polymer

A coordination polymer, metal-organic technology, applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, organic chemistry, etc., can solve the problem of catalytic activity and selectivity reduction, catalyst loading uniformity It can achieve the effect of high catalytic activity and selectivity, good stability and high catalytic activity.

Inactive Publication Date: 2015-12-09
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these traditional chiral loading methods can partly solve the problem of catalyst recovery, there are also significant reductions in catalytic activity and selectivity compared with homogeneous catalysts, low loading, poor uniformity of catalyst loading, and easy deactivation of catalysts. , low recycling times, poor load repeatability and a series of problems

Method used

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  • Novel chiral polydentate ligand, metal-organic coordination polymer formed through coordination, and application of metal-organic coordination polymer
  • Novel chiral polydentate ligand, metal-organic coordination polymer formed through coordination, and application of metal-organic coordination polymer
  • Novel chiral polydentate ligand, metal-organic coordination polymer formed through coordination, and application of metal-organic coordination polymer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The preparation of embodiment 1 compound 3a

[0073]

[0074] N 2 Under protection, add compound 1a (2.2g), compound 2 (4.5g), PdCl 2 (PPh 3 ) 2 (350mg), PPh 3 (130mg), triethylamine 10mL and tetrahydrofuran 30mL, stirred at room temperature for 1 hour. Then CuI (180mg) was added to the solution, heated to 80°C and stirred for 24h, TLC detected that compound 1a disappeared, and the reaction stopped. After purification by column chromatography, the product 3 was obtained as a yellow oil, 2.5 g, and the yield was 45%. 1 HNMR (400MHz, CDCl 3 ,298K)δ=11.92(s,1H),9.87(s,1H),8.09(d,J=1.4,1H),7.95(dd,J=15.2,9.0,2H),7.89(d,J=8.1 ,1H),7.68(d,J=1.9,1H),7.63(s,1H),7.63(d,J=1.3,1H),7.60(s,1H),7.58(s,0H),7.39–7.34 (m,1H),7.31(dd,J=8.8,1.6,1H),7.24(dd,J=6.8,1.3,1H),7.14(dd,J=8.3,6.2,2H),5.14–5.07(m ,2H),5.00(dd,J=6.8,4.4,2H),3.16(d,J=1.6,6H),1.44(s,9H). 13 CNMR (100MHz, CDCl 3 ,298K)δ=196.79,161.20,153.50,152.69,138.91,137.12,135.16,133.95,133.57,131.48,129.90,129.65,12...

Embodiment 2

[0075] The preparation of embodiment 2 compound 3b

[0076]

[0077] N 2 Under protection, add compound 1b (2.8g), compound 2 (4.5g), PdCl 2 (PPh 3 ) 2 (350mg), PPh 3 (130 mg), 10 mL of triethylamine and 30 mL of tetrahydrofuran, stirred at room temperature for 1 hour. Then CuI (180 mg) was added to the solution, heated to 80° C. and stirred for 24 h, TLC detected that compound 1b disappeared, and the reaction stopped. After purification by column chromatography, the product 3b was obtained as a yellow oil, 5.2 g, and the yield was 88%. 1 HNMR (400MHz, CDCl 3 )δ=11.86(s,1H),9.99(s,1H),8.15(d,J=1.1,1H),7.99(dd,J=11.3,9.1,2H),7.92(d,J=8.1,1H ),7.81(d,J=2.2,1H),7.68–7.62(m,5H),7.60(d,J=7.8,2H),7.42–7.35(m,2H),7.27(dd,J=6.8, 1.2,1H),7.18(dd,J=8.6,4.1,2H),5.19–5.10(m,2H),5.03(dd,J=6.8,4.0,2H),3.19(s,3H),3.19(s ,3H),1.51(s,9H). 13 CNMR (101MHz, CDCl 3 )δ=197.25,160.90,153.53,152.70,139.72,138.98,133.96,133.62,132.89,132.21,131.61,130.04,129.91,129.64,129.39,129.01,128....

Embodiment 3

[0078] The preparation of embodiment 3 compound 4a:

[0079]

[0080] Compound 3a (574 mg), 15 mL of chloroform and 3 mL of methanol were added to a 50 mL round bottom flask to form a yellow solution. 6M hydrochloric acid (3.5 mL) was added, stirred at room temperature for 6 hours, and TLC detected that the starting compound 3a disappeared. Stop the reaction, neutralize to neutral with 10% sodium carbonate solution, and separate the layers. The aqueous phase was extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain the product 4a as a yellow solid, 480 mg, with a yield of 98%. 1 HNMR (400MHz, CDCl 3 ,298K)δ=11.90(s,1H),9.84(s,1H),8.09(d,J=1.3,1H),8.00(d,J=8.9,1H),7.95(d,J=8.9,1H ),7.91(d,J=7.8,1H),7.69(d,J=2.0,1H),7.63(d,J=2.0,1H),7.44–7.36(m,4H),7.36–7.30(m, 1H), 7.14(t, J=7.9, 2H), 1.44(s, 9H). 13 CNMR (100MHz, CDCl 3 ,298K)δ=196.66,161.18,153.71,152.94,138.9...

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Abstract

The invention belongs to the technical field of heterogeneous catalysts, and specifically relates to design and synthesis of a novel chiral polydentate ligand, a novel chiral metal-organic coordination polymer, which is prepared through the coordination-driven self-assembly between the chiral polydentate ligand and a metal precursor, and an application of the polymer as a heterogeneous catalyst in asymmetric epoxide ring-opening reactions for preparing chiral amino alcohol. The provided chiral coordination polymer prepared from the chiral polydentate ligand can be used to catalyze the asymmetric epoxide ring-opening reactions so as to prepare chiral amino alcohol efficiently and high-selectively. The novel self-supported catalyst system combines the advantages of homogenous catalysis and heterogeneous catalysis, can prepare chiral amino alcohol under mild conditions, can be recycled efficiently and reused for several times, and has a good application prospect in catalytic chiral amino alcohol preparation in industry.

Description

technical field [0001] The invention belongs to the technical field of heterogeneous catalysts, and specifically relates to the design and synthesis of a class of novel chiral multi-dentate ligands, a class of novel chiral metal-organic ligands prepared by coordination self-assembly of such ligands and metal precursors. Position polymers and their application as heterogeneous catalysts in the preparation of chiral aminoalcohols by asymmetric epoxy ring-opening. Background technique [0002] Chiral amino alcohols have shown very important functions and uses in the fields of organic synthesis, chemical pharmacy, biology, and chemical industry. Many amino alcohols have good pharmacological activity and are widely used in medicine, pesticide, biology, chemical industry and so on. At the same time, chiral amino alcohol is also a chiral ligand with good coordination ability, which is commonly used in asymmetric catalysis of various organic small molecules. Therefore, the method ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C249/02C08G83/00B01J31/22C07D321/06
Inventor 涂涛孙喆明
Owner FUDAN UNIV
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