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Application of Metal Compound/Palladium Compound Catalytic Reduction System in Deallylation and Deuteration

A palladium compound and metallization technology, which is applied in the direction of organic compound/hydride/coordination complex catalyst, cyanide reaction preparation, organic compound preparation, etc., to achieve high safety, high reaction yield and small molecular weight.

Active Publication Date: 2020-12-08
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although it has been used for more than 100 years, sodium hydride is rarely used as a reducing agent, and there are few related reports

Method used

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  • Application of Metal Compound/Palladium Compound Catalytic Reduction System in Deallylation and Deuteration
  • Application of Metal Compound/Palladium Compound Catalytic Reduction System in Deallylation and Deuteration
  • Application of Metal Compound/Palladium Compound Catalytic Reduction System in Deallylation and Deuteration

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Experimental program
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Embodiment 1

[0031]

[0032] Under nitrogen protection, palladium acetate (0.018 mmol, 6 mol%) and sodium hydride (60% in oil, 0.51 mmol, 1.7 equiv) were suspended in DMA (1.0 mL), stirred at 25°C for 5 minutes, and compound 1 (0.3 mmol) was added solution in DMA (0.5 mL), then react at 25°C for 4 hours, add ice water to stop the reaction, adjust the pH value to 3.5 with dilute hydrochloric acid, extract with ethyl acetate, combine the extracts, dry with sodium sulfate, and rotate to evaporate Drying and purification by column chromatography gave product 2 with a yield of 99%. 1 HNMR (400 MHz, DMSO-d 6 ): δ 10.10 (br, 1H), 8.13 (d, J = 7.9 Hz, 1H), 7.80 (d, J = 7.7 Hz, 1H), 7.51-7.37 (m, 2H), 7.31 (q, J = 8.0 Hz, 2H), 6.87 (d, J =6.8Hz, 1H); 13 C NMR (151 MHz, DMSO-d 6 ): δ 153.12, 134.38, 127.34, 126.39,126.04, 124.53, 124.50, 121.94, 118.29, 108.00. LR-MS (ESI): m / z 145.1 [M+H] + .

Embodiment 2

[0034]

[0035]Under nitrogen protection, palladium chloride (0.006 mmol, 2 mol%) and lithium hydride (0.9 mmol, 3 equiv) were suspended in THF (1.0 mL), stirred at 25°C for 5 minutes, compound 1 (0.3 mmol) was added in THF (0.5 mL), then reacted at 80°C for 1 hour, added ice water to stop the reaction, adjusted the pH value to 3.5 with dilute hydrochloric acid, extracted with ethyl acetate, combined the extracts, dried with sodium sulfate, evaporated to dryness, and column layer Purified by analysis to obtain product 2 with a yield of 92%.

Embodiment 3

[0037]

[0038] Under nitrogen protection, Pd(MeCN) 2 Cl 2 (0.003 mmol, 1 mol%) and potassium hydride (0.3 mmol, 1 equiv) were suspended in DMF (1.0 mL), stirred at 25°C for 5 minutes, a solution of compound 1 (0.3 mmol) in DMF (0.5 mL) was added, and then in- React at 50°C for 36 hours, add ice water to stop the reaction, adjust the pH value to 3.5 with dilute hydrochloric acid, extract with ethyl acetate, combine the extracts, dry with sodium sulfate, evaporate to dryness by rotary evaporation, and purify by column chromatography to obtain the product 2, The yield is 84%.

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Abstract

The invention discloses the application of a metal compound / palladium compound catalytic reduction system in the deallylation reaction and deuteration reaction of an allyl-containing compound. The reaction comprises the following steps: under the protection of nitrogen, the palladium compound and the metal compound are suspended in a solvent Stir for 5 minutes, add allyl group-containing compound, react at -50°C to 120°C for 0.5 to 36 hours, add ice water to stop the reaction, adjust the pH value to 3.5 with dilute hydrochloric acid, and solvent extract the reaction solution, evaporate to dryness, and column Purify by chromatography to complete the reaction.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to the application of a metal hydride (deuterium) compound / palladium compound catalytic reduction system in deallylation and deuteration reactions. Background technique [0002] Sodium hydride is a strong base that is often used in laboratories and industries, and is usually used for hydrogen extraction of substrates to form corresponding sodium salts. Although it has been used for more than 100 years, sodium hydride is rarely used as a reducing agent, and there are few related reports. Until recently, several research groups reported new uses of sodium hydride as a reducing agent. For example, sodium hydride is used as a reducing agent to reduce amides to aldehydes, and bromobenzene debromination, etc., but a large excess of sodium hydride is required here, and at least 2 equivalents of sodium iodide are required as accelerators; another example is at 1,10 -...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/055C07C39/14C07C39/21C07C41/26C07C43/23C07C253/30C07C255/53C07C45/64C07C47/565C07C49/825C07C201/12C07C205/22C07D239/88C07D209/08C07C227/02C07C229/60C07C51/09C07C63/70C07C65/21C07C63/04C07D207/16C07C41/18C07C43/215
CPCC07C37/055B01J31/121B01J27/13C07C39/14
Inventor 张士磊刘晔毛玉健桂晶晶孙婉婉王柳迪
Owner SUZHOU UNIV
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