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N-heterocyclic carbene-palladium complex, and preparation method and application thereof

A technology of nitrogen heterocyclic carbene and complex, applied in the field of nitrogen heterocyclic carbene-palladium complex, can solve the problems of lack of atom economy and the like

Inactive Publication Date: 2017-06-27
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a nitrogen heterocyclic carbene-palladium complex, its preparation method and application

Method used

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  • N-heterocyclic carbene-palladium complex, and preparation method and application thereof
  • N-heterocyclic carbene-palladium complex, and preparation method and application thereof
  • N-heterocyclic carbene-palladium complex, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Example 1: Synthesis of [1,3-bis(2,6-diisopropylphenyl) imidazole-2-methylidene]-palladium chloride-isoquinoline complex (41)

[0086]

[0087] Under nitrogen protection, imidazolium salt IPr·HCl (1.1 mmol), palladium chloride (1.0 mmol), potassium carbonate (2.2 mmol), tetrahydrofuran (5.0 mL) and isoquinoline (2.0 mmol) were successively added into the reaction tube. The mixture was heated in an oil bath (80°C) for 12 hours. Stop the reaction, cool to room temperature, spin dry the solvent under reduced pressure, and separate by flash column chromatography to obtain 0.1148 g of a yellow solid product with a yield of 83%.

[0088] 1 H NMR (500MHz, CDCl 3 ,TMS)δ9.16(s,1H),8.41(d,J=6.5Hz,1H),7.77(d,J=8.5Hz,1H),7.62-7.54(m,2H),7.51-7.43(m ,3H),7.37(t,J=8.0Hz,5H),7.14(s,2H),3.32-3.12(m,4H),1.52(d,J=7.0Hz,12H),1.13(d,J= 7.0Hz,12H).

[0089] 13 C NMR (125MHz, CDCl 3) 155.1, 154.9, 146.7, 143.1, 135.6, 135.1, 131.8, 130.2, 128.2, 127.5, 126.0, 125.0, 124.0, 120.9, 2...

Embodiment 2

[0092] Example 2: Synthesis of [1,3-bis(2,6-dimethyl)imidazole-2-methylidene]-palladium chloride-isoquinoline complex (39)

[0093]

[0094] Under nitrogen protection, imidazolium salt IXy·HCl (1.1 mmol), palladium chloride (1.0 mmol), potassium carbonate (2.2 mmol), tetrahydrofuran (5.0 mL) and isoquinoline (2.0 mmol) were sequentially added into the reaction tube. The mixture was heated in an oil bath (80°C) for 12 hours. Stop the reaction, cool to room temperature, spin dry the solvent under reduced pressure, and separate by flash column chromatography to obtain 0.071 g of a yellow solid product with a yield of 61%.

[0095] 1 H NMR (500MHz, CDCl 3 ,TMS) δ9.12(s,1H,),8.33(d,J=6.0Hz,1H),7.80(d,J=8.5Hz,1H),7.65-7.59(m,2H),7.50-7.47( m,1H),7.40-7.37(m,3H),7.28-7.24(m,4H),7.12(s,2H),2.44(s,12H).

[0096] 13 C NMR (125MHz, CDCl 3 )δ154.9, 153.1, 143.1, 137.5, 136.7, 135.6, 131.8, 129.4, 128.5, 128.2, 128.1, 127.6, 126.0, 124.0, 120.9, 19.2.

[0097] Elemental analysis ...

Embodiment 3

[0099] Example 3: Synthesis of [1,3-bis(2,4,6-trimethyl)imidazole-2-methylidene]-palladium chloride-isoquinoline complex (40)

[0100]

[0101] Under nitrogen protection, imidazolium salt IMes·HCl (1.1 mmol), palladium chloride (1.0 mmol), potassium carbonate (2.2 mmol), tetrahydrofuran (5.0 mL) and isoquinoline (2.0 mmol) were sequentially added into the reaction tube. The mixture was heated in an oil bath (80°C) for 12 hours. Stop the reaction, cool to room temperature, spin dry the solvent under reduced pressure, and separate by flash column chromatography to obtain 0.0927 g of a yellow solid product with a yield of 76%.

[0102] 1 H NMR (500MHz, CDCl 3 ,TMS)δ9.13(s,1H),8.36(d,J=6.5Hz,1H),7.75(d,J=8.0Hz,1H),7.61-7.55(m,2H),7.46-7.43(m ,1H),7.36(d,J=6.0Hz,1H),7.06-7.05(m,6H),2.39(s,12H),2.36(s,6H).

[0103] 13 C NMR (125MHz, CDCl 3 )δ154.9, 152.8, 143.0, 139.0, 136.2, 135.4, 135.0, 131.7, 129.1, 128.0, 127.9, 127.5, 125.9, 124.0, 120.7, 21.1, 19.0.

[0104] Element...

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Abstract

The invention discloses an N-heterocyclic carbene-palladium complex, and a preparation method and application thereof. The N-heterocyclic carbene-palladium complex disclosed by the invention is shown in Formula (I), wherein L1 is a quinoline ligand or isoquinoline ligand, and N in the L1 is connected with Pd; L2 is an N-heterocyclic carbene ligand, and carbene carbon in the L2 is connected with the Pd; and X1 and X2 are respectively independently an anionic ligand. The N-heterocyclic carbene-palladium complex disclosed by the invention can efficiently catalyze carbon-carbon or carbon-heteroatom coupling reaction using aryl halide as a substrate. The formula is shown in the specification.

Description

technical field [0001] The invention relates to a nitrogen heterocyclic carbene-palladium complex, its preparation method and application. Background technique [0002] In recent years, nitrogen-heterocyclic carbene-palladium complexes have been widely used in organic synthesis, and they have been proven to be efficient catalysts for carbon-carbon and carbon-heteroatom constructions. In order to achieve the high catalytic efficiency of such complexes, in addition to the nitrogen heterocyclic carbene skeleton, it is necessary to find suitable auxiliary ligands in the complexes. Based on this, a series of nitrogen-heterocyclic carbene-palladium complexes containing novel auxiliary ligands have been reported. However, the current nitrogen-heterocyclic carbene-palladium complex lacks atom economy when preparing, and requires a large excess of ligands to be prepared in high yields. At the same time, the use of a large number of ligands also brings greater toxicity. . [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22C07D295/033C07D295/096C07C209/60C07C211/55C07C41/30C07C43/205C07C1/32C07C15/14
CPCC07F15/0066B01J31/2269B01J2231/4205B01J2231/4277B01J2531/004B01J2531/824C07C1/321C07C41/30C07C209/60C07C2531/22C07D295/033C07D295/096C07C211/55C07C43/205C07C15/14
Inventor 邵黎雄陆建梅刘凤
Owner WENZHOU UNIVERSITY
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