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Polyether-loaded N-heterocyclic carbene-palladium compound and preparation method and application thereof

A technology of heterocyclic carbene and palladium compounds, applied to polyether-supported N-heterocyclic carbene palladium compounds and their preparation, and the application field in the production of aryl carboxylates

Inactive Publication Date: 2010-05-05
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although people have done a lot of research on polymers used as carriers, the most common carriers are still polystyrene resins and their modifications. Up to now, there have been no reports of using polyether polymers as catalyst carriers.

Method used

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  • Polyether-loaded N-heterocyclic carbene-palladium compound and preparation method and application thereof
  • Polyether-loaded N-heterocyclic carbene-palladium compound and preparation method and application thereof
  • Polyether-loaded N-heterocyclic carbene-palladium compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] N-heterocyclic carbene palladium compound supported by polyether, the molecular formula is:

[0030]

[0031] in:

[0032] R=CH 3 ; m=10; n=1; X=Br - (1); R=CH(CH 3 ) 2 ; m=20; n=5; X=Br - (10);

[0033] R=CH 3; m=15; n=1; X=Br - (2); R=C 6 h 11 (cyclohexyl); m=10; n=1; X=Br - (11);

[0034] R=CH 3 ; m=20; n=1; X=Cl - (3); R=C 6 h 11 (cyclohexyl); m=30; n=3; X=Br - (12);

[0035] R=CH 3 ; m=25; n=1; X=Br - (4); R=C 5 h 4 N(pyridine); m=15; n=2; X=1 - (13);

[0036] R=CH 3 ; m=30; n=1; X=Br - (5); R=C 5 h 4 N(pyridine); m=25; n=3; X=Br - (14);

[0037] R=o-C 6 h 3 (CH 3 ) 2 ; m=15; n=1; X=Br - (6); R=C 6 h 7 N 2 (Dimethylpyrimidinyl); m=15; n=1; X=Br - (15);

[0038] R=o-C 6 h 3 (CH 3 ) 2 ; m=15; n=3; X=PF 6 - (7); R=C 6 h 7 N 2 (Dimethylpyrimidinyl); m=20; n=6; X=PF 6 - (16);

[0039] R=o-C 6 h 3 (CH 3 ) 2 ; m=15; n=5; X=Br - (8); R=C 2 h 5 ; m=10; n=10; X=Br - (17);

[0040] R=CH(CH 3 ) 2 ; m=15; n=2; X=Br...

Embodiment 2

[0042] Preparation of polyether-supported N-methyl-N'-oxyethylimidazolcarbene palladium compound (1):

[0043] 1) Add 1mol polyepichlorohydrin (average degree of polymerization m=15), 15mol N-methyl-N'-hydroxyethylimidazolium bromide, 15mol sodium hydride and 50ml N,N-dimethyl The formamide was stirred and dissolved, and stirred and reacted at 80°C for 48 hours; after the reaction was completed, water was added to precipitate a light yellow solid, which was washed with acetone and ether in turn, and dried in vacuum to obtain a hard solid, which was polyether-supported N-methyl-N '-Oxyethyl imidazolium bromide.

[0044] 2) Take the prepared polyether supported N-methyl-N'-oxyethyl imidazolium bromide, 15mol Pd(OAc) 2 15mol of sodium hydride was added to 50ml of N,N-dimethylformamide, stirred and refluxed at 100°C for 12h in a nitrogen atmosphere; after the reaction was completed, it was filtered, and the filter cake was washed with acetone and ether in turn, and vacuum-dried t...

Embodiment 3

[0046] Preparation of polyether-supported N-o-dimethylphenyl-N'-oxyethylimidazolcarbene palladium compound (6):

[0047] 1) Add 1mol polyepichlorohydrin (average degree of polymerization m=10), 10mol N-o-dimethylphenyl-N'-hydroxyethyl imidazolium bromide, 10mol sodium tert-butoxide and 50ml N , N-dimethylformamide was stirred and dissolved, and stirred and reacted at 100°C for 32 hours; after the reaction was completed, water was added to precipitate a light yellow solid, which was washed with acetone and ether in turn, and a hard solid was obtained after vacuum drying, which was polyether-loaded N-o-dimethylphenyl-N'-oxyethylimidazolium bromide.

[0048] 2) Load N-o-dimethylphenyl-N'-oxyethyl imidazolium bromide, 10mol PdCl 2 Add 10mol sodium tert-butoxide to 50ml N,N-dimethylformamide, stir and reflux at 110°C for 10h in a nitrogen atmosphere; filter after the reaction, wash the filter cake with acetone and ether in turn, and vacuum dry to obtain Product (6), yield 73.2%. ...

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Abstract

The invention relates to a polyether-loaded N-heterocyclic carbene-palladium compound and a preparation method and application thereof, belonging to the field of organic synthesis. For the polyether-loaded N-heterocyclic carbene-palladium compound, polyether molecular chains contain chain links (I): n in the chain links (I) is equal to 1-10, R is aryl or alkyl, and X is Cl-, Br-, I-, BF4- or PF6-. Compared with polyvinyl benzene, the polyether compound has good main chain flexibility and adjustable branched chain length, and can be used for loading a catalyst to enable the catalyst to maintain higher catalytic activity and enable polymers containing polyepichlorohydin chain links, N-hydroxyl-substituted imidazolium, alkali and palladium salts to react to prepare the compound. The invention also provides the application of the compound: the compound is used for catalyzing substituting reaction of aromatic compounds Aryl-X' and alpha-H contained carboxylic ester to synthesize alpha-aryl carboxylic ester by one-step catalysis, and has mild reaction condition, high yield, good economic benefit and important application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a polyether-loaded N-heterocyclic carbene palladium compound and a preparation method thereof, and also relates to the application of the compound in the production of aryl carboxylates. Background technique [0002] Aryl carboxylate compounds have anti-inflammatory and analgesic effects, and are important structural units of many natural products, drugs, and synthetic intermediates, and have a wide range of applications. With the rapid development of industrial economy, the demand for aryl carboxylate derivatives in various related industries will also increase. At present, there are many synthetic methods of aryl carboxylate compounds, but only sodium cyanide method, phenylacetamide method and carbon monoxide oxo synthesis method have real industrial value. More than 90% of enterprises in my country use the traditional sodium cyanide method, but this method has disa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/337C08G65/338C07F15/00B01J31/12B01J31/06C07C67/343C07C69/614C07C69/734C07C69/616C07C69/612
Inventor 徐晨李红梅王苏静赵新杰岑非非张玉清
Owner LUOYANG NORMAL UNIV
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