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Tridentate carbene, and preparation method and application thereof

A technology of carbene and carbene complexes, which is applied in the preparation of carboxylic acid nitrile, the preparation of halogenated hydrocarbons, chemical instruments and methods, etc., can solve the problem that tridentate bicarbene ligands have not been reported.

Inactive Publication Date: 2019-08-06
RENMIN UNIVERSITY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are no reports about tridentate bicarbene ligands and their complexes

Method used

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  • Tridentate carbene, and preparation method and application thereof
  • Tridentate carbene, and preparation method and application thereof
  • Tridentate carbene, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The present embodiment prepares the compound shown in formula [a], comprises the following steps:

[0088] 1) 1,3-bis(1,3-bis(2,6-diisopropyl-benzene)-1,2,3-triazole)-dimethylamine salt (L 2 ) preparation

[0089] Add potassium hexafluorophosphate (1.9g, 10.4mmol) into a 250mL schlenk bottle, heat and pump for N 2 Several times, add 1,3-bis(2,6-diisopropyl-benzene)-triazene (5.0 g, 13.4 mmol) after the schelenk bottle is cooled, and ventilate three times, then cool down to -78 ° C, Add 50 mL of ultra-dry dichloromethane, add BOC-protected dipropynylamine (10 g, 5.2 mmol), and after the temperature is stabilized at -78 ° C, protect from light, add t BuOCl (1.30mL, 11.4mmol), heated by itself overnight. Suction filter in a ventilated place, wash the solid with dichloromethane, collect the filtrate, and remove the dichloromethane by rotary evaporation to obtain a white solid. Then add 100mL diethyl ether to wash to obtain white solid L 1 3.98 g, yield: 63%.

[0090]...

Embodiment 2

[0101] Compound shown in the present embodiment preparation formula [b]

[0102] In Example 1, 1,3-bis(2,6-diisopropyl-benzene)-triazene was replaced by 1,3-bis(2,4,6-trimethyl-benzene)-tri Nitrogen, the rest of the conditions are the same as in Example 1 to obtain the compound shown in formula [b].

[0103] The compound shown in the formula [b] prepared in embodiment 2 can be passed through proton nuclear magnetic resonance spectrum ( 1 (HNMR) test to verify its structure, characterized as follows:

[0104] 1 HNMR (CDCl 3 ,400MHz,δppm)δ7.06(s,4H),7.05(s,4H),4.00(s,4H),2.36(d,J=2.4Hz,12H),2.15(s,12H),2.09(s ,12H).

Embodiment 3

[0106] The present embodiment prepares the compound shown in formula [c], comprises the following steps:

[0107] 1)L 4 preparation of

[0108] DMSO:H in an oven-dried 100 mL schlenk bottle 2 O (9:1) mixed solution was added with 1-phenyl-azidobenzene (0.68g, 5.7mmol) and cuprous iodide (0.099g, 0.5mmol) and stirred for 10 minutes. BOC-protected dipropynylamine (0.5 g, 2.6 mmol) was added and stirred for another 24 hours, the reaction mixture was added to ice water, a solid precipitated out, the solvent was filtered off, the precipitate was washed with water and acetone, and dried under vacuum to obtain a white solid L 3 0.98g, Yield: 87%.

[0109] Add L to the dried 100mL schlenk bottle 3 (86.3mg, 0.2mmol), and added 5mL of ultra-dry dichloromethane, cooled to -78°C, then added methyl trifluoromethanesulfonate (72.2mg, 0.44mmol), when the reaction rose to room temperature, added trifluoromethane Sulfonic acid (75.0mg, 0.50mmol) was extracted with dichloromethane after r...

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Abstract

The invention provides a tridentate carbene, and a preparation method and an application thereof. The tridentate carbene has a structure represented by formula [1]; and in the formula [1], R1 and R2 are independently selected from substituted or unsubstituted C1-10 chain alkyl groups, C3-10 cycloalkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups and aryl groups. The tridentate carbene has astrong catalytic performance, and can be used in various reactions as a catalyst, and the preparation method is simple and easy.

Description

technical field [0001] The invention relates to a tridentate carbene and its preparation method and application, belonging to the technical field of organic catalysis. Background technique [0002] Since N-heterocyclic carbene is similar to electron-rich phosphine ligands, and metal carbene bonds have good thermal stability, water resistance and oxidation resistance, N-heterocyclic carbene can replace unstable The use of phosphine ligands in catalytic reactions has attracted widespread attention from scientists. [0003] In 1995, Herrmann et al. first reported the application of N-heterocyclic carbene transition metal compounds in catalytic reactions, and realized that this type of metal compounds had superior catalytic properties. Since then, N-heterocyclic carbene has been rapidly developed in the field of organometallic synthesis and homogeneous catalysis, and has become one of the research hotspots in the field of organic chemistry. [0004] However, there are no repor...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D249/04C07F15/00C07F15/04C07F1/12C07F1/08B01J31/02B01J31/22C07C41/30C07C43/205C07C201/12C07C205/06C07C253/30C07C255/50C07C17/263C07C22/08
CPCB01J31/0244B01J31/2273B01J2231/4211B01J2531/16B01J2531/18B01J2531/824B01J2531/847C07C17/263C07C41/30C07C201/12C07C253/30C07D249/04C07D249/06C07F1/08C07F1/12C07F15/006C07F15/04C07C43/205C07C205/06C07C255/50C07C22/08
Inventor 闫晓宇李林峰顼兴宇
Owner RENMIN UNIVERSITY OF CHINA
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