Ring enlargement azoheterocyclic carbene-palladium compound containing picolyl

A technology of heterocyclic carbene and pyridine methyl is applied to pincer-shaped ring-expanded nitrogen heterocyclic carbene palladium compound and its application field in catalyzing C-N coupling reaction, and achieves high-efficiency catalytic performance, high catalytic yield and short reaction time Effect

Active Publication Date: 2015-07-01
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tridentate coordinated pincer ring-expanded nitrogen heterocyclic carbene metal compounds have not been reported

Method used

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  • Ring enlargement azoheterocyclic carbene-palladium compound containing picolyl
  • Ring enlargement azoheterocyclic carbene-palladium compound containing picolyl
  • Ring enlargement azoheterocyclic carbene-palladium compound containing picolyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a 100mL round-bottomed flask, mix pyridine-2-carbaldehyde (30mmol, 3.21g) and 1,3-propylenediamine (15mmol, 1.11g) in 30mL of methanol, react at room temperature for 5.0 hours, and slowly Add NaBH 4 (120mmol, 4.54g), the temperature was slowly raised to 70°C for 5 hours, cooled to room temperature, and the reaction solution was spin-dried. Then use 50mL CH 2 Cl 2 Dissolved, filtered, and the filtrate was spin-dried to obtain a yellow oily sticky substance. After dissolving the above-mentioned yellow oily viscous substance in 30 mL of methanol, an equimolar amount of formaldehyde aqueous solution was added thereto, and after stirring at room temperature for 3 hours, the solvent was removed under reduced pressure, separated and purified by column chromatography to obtain 1,3-bis(2-pyridylmethyl) Hexahydropyrimidine (3.50 g, 87% yield).

[0032] In a 100mL round bottom flask, 1,3-bis(2-pyridylmethyl)hexahydropyrimidine (5mmol, 1.34g) was dissolved in 30mL of ethylen...

Embodiment 2

[0035] Mix pyridine-2-carbaldehyde (30mmol, 3.21g) and 2,2-dimethyl-1,3-propanediamine (15mmol, 1.53g) in 30mL methanol, react at room temperature for 7.0 hours, and stir in an ice-water bath Add NaBH slowly 4 (120mmol, 4.54g), slowly warming up to 70°C for 5 hours. The reaction was stopped, cooled to room temperature, and the reaction solution was spin-dried. Then use 50mL CH 2 Cl 2 Dissolved, filtered, and the filtrate was spin-dried to obtain a yellow oily viscous substance. After dissolving the above-mentioned yellow oily viscous substance in 30 mL of methanol, an equimolar amount of formaldehyde aqueous solution was added thereto, and after stirring at room temperature for 3 hours, the solvent was removed under reduced pressure, separated and purified by column chromatography to obtain 3,3-dimethyl-1,3 - Bis(2-pyridylmethyl)hexahydropyrimidine (3.96 g, 89% yield).

[0036] Dissolve 3,3-dimethyl-1,3-bis(2-pyridylmethyl)hexahydropyrimidine (5mmol, 1.48g) in 30mLDME, th...

Embodiment 3

[0039] Mix 5-bromopyridine-2-carbaldehyde (30mmol, 5.58g) and 1,3-propanediamine (15mmol, 1.11g) in 30mL of methanol, react at room temperature for 5.0 hours, slowly add NaBH under ice-water bath stirring 4 (120mmol, 4.54g), slowly warming up to 70°C for 5 hours. The reaction was stopped, cooled to room temperature, and the reaction solution was spin-dried. Then use 50mL CH 2 Cl 2 Dissolved, filtered, and the filtrate was spin-dried to obtain a yellow oily viscous substance. After dissolving the above-mentioned yellow oily viscous substance in 30 mL of methanol, an equimolar amount of formaldehyde aqueous solution was added thereto, and after stirring at room temperature for 3 hours, the solvent was removed under reduced pressure, separated and purified by column chromatography to obtain 1,3-bis(5-bromo-2 -Pyridylmethyl)hexahydropyrimidine (5.30 g, 83% yield).

[0040] 1,3-bis(5-bromo-2-pyridylmethyl)hexahydropyrimidine (5mmol, 2.13g) was dissolved in 30mL DME, and NBS (5m...

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Abstract

The invention belongs to the field of organic compounds, and relates to a pincer ring enlargement azoheterocyclic carbene-palladium compound. The pincer ring enlargement azoheterocyclic carbene-palladium compound has a structure shown in the specification. The pincer ring enlargement azoheterocyclic carbene-palladium compound disclosed by the invention provides a kind of novel metal catalyst for C-N coupled reaction; when being used for catalyzing the C-N coupled reaction, the pincer ring enlargement azoheterocyclic carbene-palladium compound is short in reaction time, low in use amount of the catalyst, simple to operate and high in catalytic yield; alkali cheap and easy to obtain is used; and a reaction solvent is unnecessary to process.

Description

technical field [0001] The invention belongs to the field of organic compounds, and relates to a pincer ring-expanding nitrogen-heterocyclic carbene palladium compound and its application in catalyzing C-N coupling reactions. Background technique [0002] N-heterocyclic carbenes (N-Heterocyclic Carbenes, NHCs) and their metal compounds are mostly used in the research fields of organometallic chemistry, coordination chemistry, homogeneous catalysis, materials chemistry and medicinal chemistry. Current research focuses on five-membered nitrogen heterocyclic carbene (five-NHCs) and its metal compounds, including imidazole-derived classic imidazole-2-carbene metal compounds, imidazoline-2-carbene metal compounds (A-D) and Professor Crabtree The non-classical carbene metal compound (E-F) represented by imidazole-4-carbene was reported by the research group for the first time. [0003] [0004] Imidazole-derived five-membered-NHCs-metal compounds [0005] Tridentate pincer ni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22C07D295/033C07D213/74C07D401/04C07D403/04C07D235/18C07D239/42
CPCB01J31/2273B01J2231/4277B01J2531/824C07D213/74C07D235/08C07D239/42C07D295/023C07D295/033C07D401/04C07D403/04C07F15/006
Inventor 杨亮茹买文鹏毛璞肖咏梅袁金伟屈凌波
Owner HENAN UNIVERSITY OF TECHNOLOGY
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