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Heterogeneous chiral bifunctional catalyst as well as preparation method and application thereof

A bifunctional catalyst, heterogeneous technology, used in catalyst activation/preparation, carbon-based compound preparation, chemical instruments and methods, etc. Catalyst synergy and other issues, to achieve good catalytic activity and cycle stability, excellent enantioselectivity, and improve the effect of activity and stereoselectivity

Pending Publication Date: 2022-07-29
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the coordination of organocatalysts with metal clusters or MOF ligands will segment the catalysts into different regions, severely limiting the freedom and flexibility of organocatalysts in catalytic reactions.
This would greatly reduce the synergy between catalysts, thereby limiting the activity and stereoselectivity, especially for synergistic asymmetric catalytic reactions.
Therefore, at present, the known bifunctional catalysts generally have low activity and low stereoselectivity, which cannot meet the requirements of industrial production.

Method used

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  • Heterogeneous chiral bifunctional catalyst as well as preparation method and application thereof
  • Heterogeneous chiral bifunctional catalyst as well as preparation method and application thereof
  • Heterogeneous chiral bifunctional catalyst as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 1. Preparation of CP@Pd@MOF-808

[0045] (1) Sodium hydride (751 mg, 18.77 mmol) and anhydrous tetrahydrofuran (THF) (20 mL) were added to a round bottom flask filled with nitrogen, and stirred at 0° C. for 10 min. Trans-boc-4-hydroxy-l-proline solution (2.0 g, 8.65 mmol) was then added dropwise to anhydrous THF (30 mL). With continued stirring, 4-chloromethylstyrene (90%, 3.66 g, 21.6 mmol) was added slowly over 1 h. The resulting mixture was then heated to 50°C and stirred overnight. After the reaction was cooled to room temperature, water (30 mL) was added and extracted three times with cyclohexane (50 mL). Join KHSO 4 The solution was adjusted to pH=2, then extracted three times with ether (50 mL), anhydrous MgSO 4 dry. After being concentrated in vacuo, separated and purified by column chromatography to obtain a yellow oily chiral macromolecular monomer whose structural formula is as follows:

[0046]

[0047] (2) MOF-808 is the H 3 BTC (127mg, 0.605mmol)...

Embodiment 2

[0067] (1) Sodium hydride (18.77 mmol) and anhydrous tetrahydrofuran (THF) (10 mL) were added to a round bottom flask filled with nitrogen, and stirred at 0° C. for 10 min. Trans-boc-4-hydroxy-l-proline solution (5.61 mmol) was then added dropwise to dry THF (20 mL). With continued stirring, 4-chloromethylstyrene (18.7 mmol) was added slowly over 1 h. The resulting mixture was then heated to 50°C and stirred overnight. After the reaction was cooled to room temperature, water (30 mL) was added and extracted three times with cyclohexane (50 mL). Join KHSO 4 The solution was adjusted to pH=2 in the aqueous phase, then extracted three times with ether (50 mL), anhydrous MgSO 4 dry. After vacuum concentration, separation and purification by column chromatography gave a yellow oily chiral polymer monomer.

[0068] (2) MOF-808 is the H 3 BTC (127mg, 0.605mmol), ZrOCl 2 8H 2 O (195 mg, 0.605 mmol), deionized water (4 mL) and trifluoroacetic acid (1.38 g, 12.1 mmol) were added...

Embodiment 3

[0072] (1) Sodium hydride (751 mg, 18.77 mmol) and anhydrous tetrahydrofuran (THF) (30 mL) were added to a round bottom flask filled with nitrogen, and stirred at 0° C. for 10 min. Trans-boc-4-hydroxy-l-proline solution (16.83 mmol) was then added dropwise to dry THF (40 mL). With continued stirring, 4-chloromethylstyrene (28.1 mmol) was added slowly over 1 h. The resulting mixture was then heated to 50°C and stirred overnight. After the reaction was cooled to room temperature, water (30 mL) was added and extracted three times with cyclohexane (50 mL). Join KHSO 4 The solution was adjusted to pH=2 in the aqueous phase, then extracted three times with ether (50 mL), anhydrous MgSO 4 dry. After vacuum concentration, separation and purification by column chromatography gave a yellow oily chiral polymer monomer.

[0073] (2) MOF-808 is the H 3 BTC (127mg, 0.605mmol), ZrOCl 2 8H 2 O (585 mg, 1.815 mmol), deionized water (5 mL) and trifluoroacetic acid (2.7 g, 17.8 23.7 mmo...

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PUM

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Abstract

The invention discloses a heterogeneous chiral bifunctional catalyst as well as a preparation method and application thereof, the heterogeneous chiral bifunctional catalyst is CP (at) Pd (at) MOF-808, and is formed by in-situ polymerization or reduction of a chiral polymer monomer and Pd < 2 + > salt in a pore channel of the MOF-808. The chiral flexible high polymer material is used as the carrier of the chiral catalyst, so that the prepared chiral catalyst can keep certain flexibility, flexibility and degree of freedom on the rigid MOF-808 carrier, and the activity and stereoselectivity of the catalyst are improved. The prepared CP (at) Pd (at) MOF-808 has good catalytic activity and cycling stability. The CP (at) Pd (at) MOF-808 synthesized by the method disclosed by the invention shows relatively high coupling and co-production rate and excellent enantiomer selectivity in a one-pot Suzuki coupling-asymmetric aldol condensation continuous reaction.

Description

technical field [0001] The invention relates to a heterogeneous chiral bifunctional catalyst, a preparation method and application thereof, and belongs to the technical field of organic catalytic chemistry. Background technique [0002] Inspired by enzymatic catalysis, small-molecule asymmetric catalysis is a sustainable green chemistry approach that plays a key role in the synthesis of fine chemicals and drugs, and is more convenient, economical, and environmentally friendly than traditional enzymatic catalysis. In recent years, small molecule organocatalysts have developed rapidly, but there are also some defects, such as the recovery and utilization of catalysts. Immobilizing various catalysts on supports is an ideal strategy to ensure the heterogeneous catalysis and recyclability of catalysts, and many methods for immobilizing catalysts have been reported, such as covalent attachment, or encapsulating catalysts in the cavities of porous solids. middle. But the activity...

Claims

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Application Information

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IPC IPC(8): B01J31/22B01J31/06B01J37/16B01J35/10C07C45/68C07C47/546C07C45/72C07C49/747
CPCB01J31/1691B01J31/2239B01J31/062B01J37/16C07C45/68C07C45/72B01J2531/48B01J2231/4211B01J2231/342C07C2601/08B01J35/40B01J35/617B01J35/633C07C47/546C07C49/747Y02P20/584
Inventor 李一鸣
Owner SOUTHEAST UNIV
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