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First-class porous organic polymer containing phosphine ligand as well as preparation method and application of first-class porous organic polymer

A technology for phosphine ligands and polymers is applied in the field of porous polymers containing bidentate phosphoramidite phosphine ligands and their preparation, which can solve the problems of easy generation of hydrogenated products and low catalyst activity, and achieve good selectivity and recyclability. , the preparation method is simple, the effect of high catalytic rate

Active Publication Date: 2019-10-15
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are still many difficulties to be overcome in this type of reaction: first, hydrogenation products are easily generated in the reaction; second, the regioselectivity and stereoselectivity of the reaction need to be improved; third, the activity of the catalyst is low; fourth, Catalyst recycling issues have not been resolved

Method used

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  • First-class porous organic polymer containing phosphine ligand as well as preparation method and application of first-class porous organic polymer
  • First-class porous organic polymer containing phosphine ligand as well as preparation method and application of first-class porous organic polymer
  • First-class porous organic polymer containing phosphine ligand as well as preparation method and application of first-class porous organic polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The vinyl binaphthol used in the following examples is prepared by the following method, specifically:

[0042] Vinyl binaphthol preparation of

[0043] Under nitrogen protection, add raw materials to the reaction flask 500mg, C 2 h 3 BF3 K (664 mg, 4.9 mmol), THF (6 mL) and water (1 mL), heated to reflux for 24 hours, and the product was separated and purified by column chromatography. The obtained product (200 mg), methanol (6.2 mL), water (3.1 mL) and saturated NaHCO 3 (6.2 mL) was further added into the reaction flask, and the mixture was heated to 50° C. and reacted for 5 hours. The obtained crude product was separated and purified by column chromatography to obtain vinyl biphenol. The product is characterized as follows: 1 H NMR (500MHz, CDCl 3 )δ7.95(d, J=10.0Hz, 2H), 7.83(s, 2H), 7.49(d, J=10.0Hz, 2H), 7.39(d, J=10.0Hz, 2H), 7.13(d, J=10.0Hz, 2H), 6.88(dd, J=20.0, 10.0Hz, 2H), 5.82(d, J=20.0Hz, 2H), 5.32(d, J=10.0Hz, 2H), 5.16(s, 2H)ppm.

Embodiment 2

[0045] synthesis

[0046] Under argon atmosphere, add dipyrrole phosphorus chloride (131.0mg, 1.9mmol), anhydrous triethylamine (0.09mL, 0.69mmol) and anhydrous tetrahydrofuran (6mL) respectively into a 100mL Schlenk tube, cool to 0°C , add dropwise 6,6'-divinyl-2,2'-binaphthyldiol (112mg, 0.35mmol) anhydrous tetrahydrofuran (6mL) solution, slowly warming up to room temperature and stirring overnight, stop the reaction, spin off the solvent under reduced pressure, column chromatography (eluent: ethyl acetate: petroleum ether = 1 / 10) 203.3 mg of a colorless oil was isolated with a yield of 88%. 1 H NMR (CDCl 3 ,500MHz): δ7.92(d,J=7.0Hz,2H),7.87(s,2H),7.33(d,J=8.0Hz,2H),7.07(s,2H),7.24-7.20(m, 2H), 6.96-6.90(m, 2H), 6.58(d, J=25.0Hz, 8H), 6.20(d, J=25.0Hz, 8H), 5.88(d, J=17.0Hz, 2H), 5.39( d,J=11.5Hz,2H)ppm. 13 C NMR (125MHz, CDCl 3 ): δ149.2(d, J=12.0Hz), 136.4, 134.5, 133.2, 130.9, 130.5, 126.3, 126.0, 124.5, 122.5, 121.0(d, J=14.4Hz), 120.9(d, J=13.9Hz ), 119.5(d, J...

Embodiment 3

[0048] Polymer I 1 synthesis

[0049] Under a nitrogen atmosphere, anhydrous tetrahydrofuran (11.0 mL) was added to a 50 mL stopcock bottle, and the copolymerization unit (225.0mg, 0.34mol) and (460.0 mg, 1.36 mmol). Finally 25.0 mg of initiator AIBN was added. After stirring at room temperature for 10 min, react at 100°C for 24 h, the product was separated by centrifugation, washed with tetrahydrofuran (3×10 mL) and rotary evaporated to obtain a white solid (640.0 mg).

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PUM

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Abstract

The invention discloses a first-class porous organic polymer containing a phosphine ligand as well as a preparation method and application of the first-class porous organic polymer. The polymer comprises the following formula I; the polymer is prepared by polymerizing compounds in the formula. After reacting with transition metal salt to generate a catalyst, the porous organic polymer containing the phosphine ligand is used for catalyzing hydroformylation reaction of alkyne; the porous organic polymer containing the phosphine ligand is high in catalyzing rate, high in selectivity and cycling performance and high in practical value.

Description

technical field [0001] The invention relates to a class of porous organic polymers containing phosphine ligands, a preparation method and application thereof. Specifically, it relates to a class of porous polymers containing bidentate phosphoramidite phosphine ligands and a preparation method thereof. The polymer-loaded rhodium catalyst can efficiently catalyze the hydroformylation reaction of alkynes, and belongs to the technical field of organic chemistry. [0002] technical background [0003] Hydroformylation refers to alkenes and CO / H 2 The process of forming aldehydes under the action of a catalyst. Compared with the hydroformylation of alkenes, the hydroformylation of alkynes is less studied. The hydroformylation reaction of alkynes refers to alkynes and CO / H 2 The process of generating α,β-unsaturated aldehydes under the action of a catalyst. Synthesized α,β-unsaturated aldehydes play an important role in the preparation of perfumes and organic synthesis. So far,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F230/02C08F212/08C08F212/34B01J31/24C07C45/50C07C47/232C07C47/277C07C47/24C07C49/86C07C47/21
CPCC08F230/02C08F212/08C08F212/34B01J31/2442C07C45/50C07C45/505C07B2200/09B01J2531/822B01J2231/321C07C47/232C07C47/277C07C47/24C07C49/86C07C47/21
Inventor 贾肖飞宗玲博梁祖宇
Owner QINGDAO UNIV OF SCI & TECH
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