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Halogenated 1,2,3-triazolecarbene and its preparation method and application

A technology of triazole carbene and triazole carbene, applied in the field of organic catalysis, can solve problems such as limiting the development of triazole carbene

Inactive Publication Date: 2021-06-08
RENMIN UNIVERSITY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, in the reports on the research on triazole carbene, there are few reports on the modification of triazole salt carbene complexes, such as the introduction of modified functional groups at the ortho position of the carbene, thus limiting the development of triazole carbene

Method used

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  • Halogenated 1,2,3-triazolecarbene and its preparation method and application
  • Halogenated 1,2,3-triazolecarbene and its preparation method and application
  • Halogenated 1,2,3-triazolecarbene and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0101] Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-chloro-1,2,3-triazolecarbene

[0102] 1) Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-chloro-1,2,3-triazole salt

[0103] In a Shrek bottle at -78°C under nitrogen protection, 3.6 g (10 mmol) of 1,3-bis(2,6-diisopropyl-benzene)-triazene, 2 g (11 mmol) of potassium hexafluorophosphate, and ), 30ml of dichloromethane, 1mL (mmol) of 1,1-dichloroethylene and 1.7mL (15mmol) of tert-butyl hypohalite were added in the dark. Allow to warm to room temperature freely. After that, water was added for washing, and after washing with water three times, the organic phase was dried. The organic solvent was removed by rotary evaporation, and the obtained solid was washed three times with ether. After washing off most of the black matter, it was recrystallized with dichloromethane and ether to obtain 1,3-bis(2,6-diisopropyl-benzene )-5-chloro-1,2,3-triazole salt. After weighing, 1,3-bis(2,6-diisopropyl-benzene)-5-chloro-1,2,3-tr...

Embodiment 2

[0109] Preparation of 1,3-bis(2,6-diisopropyl-phenyl)-5-bromo-1,2,3-triazolecarbene

[0110] 1) Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-bromo-1,2,3-triazole salt

[0111] In a Shrek bottle at -78°C under nitrogen protection, 3.6 g (10 mmol) of 1,3-bis(2,6-diisopropyl-benzene)-triazene, 2 g (11 mmol) of potassium hexafluorophosphate, and ), 30 mL of dichloromethane, 0.8 mL (10 mmol) of 1,2-dibromoethylene and 1.7 mL (15 mmol) of tert-butyl hypohalite were added in the dark. Let it warm up to room temperature naturally. After that, water was added for washing, and after washing with water three times, the organic phase was dried. The organic solvent was removed by rotary evaporation, and the obtained solid was washed three times with ether. After washing off most of the black matter, it was recrystallized with dichloromethane and ether to obtain 1,3-bis(2,6-diisopropyl-benzene )-5-bromo-1,2,3-triazole salt. After weighing, 1,3-bis(2,6-diisopropyl-benzene)-5-bromo-1...

Embodiment 3

[0119] Preparation of 1,3-bis(2,6-diisopropyl-phenyl)-5-fluoro-1,2,3-triazolecarbene

[0120] 1) Preparation of 1,3-bis(2,6-diisopropyl-benzene)-5-fluoro-1,2,3-triazole salt

[0121] In a Shrek bottle at -78°C under nitrogen protection, 3.6 g (10 mmol) of 1,3-bis(2,6-diisopropyl-benzene)-triazene, 2 g (11 mmol) of potassium hexafluorophosphate, and ), 30 mL of dichloromethane, 0.8 mL (10 mmol) of 1,2-difluoroethylene and 1.7 mL (15 mmol) of tert-butyl hypohalite were added in the dark. Let it warm up to room temperature naturally. After that, water was added for washing, and after washing with water three times, the organic phase was dried. The organic solvent was removed by rotary evaporation, and the obtained solid was washed three times with ether. After washing off most of the black matter, it was recrystallized with dichloromethane and ether to obtain 1,3-bis(2,6-diisopropyl-benzene )-5-fluoro-1,2,3-triazole salt. After weighing, 1,3-bis(2,6-diisopropyl-benzene)-5-flu...

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Abstract

The present invention provides a halogenated 1,2,3-triazole carbene and its preparation method and application, which has the structure of formula [1]: wherein, R 1 and R 2 are independently selected from substituted or unsubstituted aryl groups; X represents halogen. It has strong catalytic performance, can be used as a catalyst in various reactions, and the preparation method is simple and feasible.

Description

technical field [0001] The invention relates to a halogenated 1,2,3-triazole carbene and its preparation method and application, belonging to the technical field of organic catalysis. Background technique [0002] Carbenes are an important class of ligands that can be used in important fields such as organic catalysis. Among them, triazole carbene as a nitrogen heterocyclic carbene can catalyze many reactions, such as polymerization reaction, reaction of unsaturated aldehyde and ketone, reaction of alcohol and aldehyde, Stette asymmetric reaction, nucleophilic acylation reaction, benzoin condensation reaction, aldehyde and Imine reaction, ketone and benzoin type compound reaction, transesterification reaction, etc. Meanwhile, triazole carbene complexes can be used for olefin metathesis reaction, Kumada coupling reaction, Suzuki reaction and Stille reaction, Heck reaction, catalytic furan synthesis reaction, intramolecular hydroamination reaction, cyclopropanation reaction, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/06C07F1/08B01J31/02B01J31/22C07C45/72C07C49/83
CPCB01J31/0244B01J31/2273B01J2231/328B01J2231/4277B01J2531/16C07C45/72C07D249/06C07F1/08C07C49/83
Inventor 闫晓宇顼兴宇李林峰
Owner RENMIN UNIVERSITY OF CHINA
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