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New photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds

A new method, photocatalytic technology, applied in the direction of organic chemical methods, chemical instruments and methods, carbon-based compound preparation, etc., can solve the problem of low selectivity

Active Publication Date: 2019-01-11
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It aims to solve the key problems of traditional deuterium addition reaction, such as the need to use deuterium gas, high temperature, high pressure conditions, and low selectivity

Method used

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  • New photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds
  • New photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds
  • New photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0049] (1) Preparation of photocatalytic materials

[0050] The photocatalytic material is taken as an example of palladium (Pd)-loaded carbon nitride (PCN), and its preparation method is as follows:

[0051] Mix 2 g of melamine and 20 g of potassium bromide evenly and grind for 5 minutes, transfer to an alumina ceramic crucible, place it in a tube furnace, set the roasting program, and heat up to 550°C for 2 hours. Naturally cooled to room temperature, the obtained yellow solid was dispersed in 200 mL of 80°C hot water, stirred for 30 minutes, filtered while hot, and washed three times with deionized water. The obtained carbon nitride solid was dried in an oven at 80 degrees for 24 hours for later use.

[0052] Take 0.3 g of the above-mentioned carbon nitride solid, disperse it in 80 mL of deionized water, add 20 mL of ethylene glycol solution, stir and sonicate for 2 hours. Add 28 μL, 1 mol / L chloropalladium acid solution to the obtained mixed liquid with a pipette, and re...

Embodiment 1

[0055] Embodiment 1: the photocatalytic hydrogenation reaction of styrene

[0056]

[0057] Weigh 0.1mmol styrene, 0.1mmol AlCl respectively 3 , 10.0mg of Pd / PCN photocatalyst was added to a 5mL reaction flask, and a mixed solution of ethyl acetate / water / methanol (2mL / 1.5mL / 1.5mL) was added to replace the reaction system into an argon protection state, and then the reaction The bottle was placed under a 420nm light source for light reaction for 4 hours. After the reaction was completed, the light source was removed, and the reaction mixture was washed with 5.0mL CH 2 Cl 2 After extraction, the extract was dried over anhydrous sodium sulfate and concentrated to obtain a colorless liquid. GC-MS analysis was performed and the yield of the reaction was determined in conjunction with a standard curve of the target product.

[0058] According to the same synthesis method, other compounds can be catalytically hydrogenated to obtain corresponding hydrogenated products, see Table...

Embodiment 14

[0063] Example 14: Preparation of deuterated chemicals by photocatalytic deuterium addition of (E)-1,2-stilbene with deuterium water as deuterium source

[0064]

[0065] Weigh 0.1mmol (E)-1,2-stilbene, 0.1mmol AlCl 3 , 10.0mg of Pd / PCN nanosheets were added to a 5mL reaction bottle, and a mixed solution of ethyl acetate / deuterium water / deuterated methanol (2mL / 1.5mL / 1.5mL) was added with a syringe to replace the reaction system into an argon protection state , and then the reaction bottle was placed under a 420nm light source for 4.0 hours of light reaction. After the reaction, the light source was removed, and the reaction mixture was washed with CH 2 Cl 2 (5.0mL×3) extraction, combined organic phases, dried with anhydrous sodium sulfate, vacuum desolvated, column chromatography separation to obtain the target product. The resulting product was analyzed by GC-MS, HRMS, 1 HNMR, C-NMR, FT-IR and other tests to confirm the structure.

[0066] According to the same synthe...

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Abstract

The invention relates to a new photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds. The method is characterized in that an olefin or alkyne compound and a deuterium source undergoes a deuteration reaction under the catalysis of a light source and a photocatalyst to obtain a deuterated product, wherein the deuterium source is deuterated water, deuterated alcohol or deuterated acid, and the reaction temperature is between room temperature and 80 DEG C. The fixed-point deuteration reaction of the olefin or alkyne compound is realized under the photocatalysis action of the photocatalyst with environmentally-friendly and cheap deuterated water or a deuteration reagent as a deuterium source to substitute deuterium gas. Compared with traditional deuteration reactions, the method has a higher selectivity, milder reaction conditions and higher economical suitability, and is suitable for large-scale deuterated chemical substance production.

Description

technical field [0001] The invention relates to the field of photocatalytic preparation of chemicals, in particular to a method for realizing a fixed-point deuteration reaction of carbon-carbon unsaturated bonds by using a clean deuterium source and photocatalytic technology. Background technique [0002] Deuterated chemicals are a special class of compounds that have important applications in the fields of reaction mechanism research, kinetics, drug metabolism, and biological structure determination. Heavy isotopes of hydrogen (deuterium or tritium) are usually introduced into the target compound through a multi-step synthesis. The currently commonly used hydrogen-deuterium exchange reaction is a very attractive strategy, but this method faces great challenges. On the one hand, the hydrogen-deuterium exchange reaction often uses deuterium gas as the deuterium source, and most processes involve high temperature, high pressure, strong acid, and strong alkali conditions; sit...

Claims

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Application Information

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IPC IPC(8): C07C5/03C07C45/67C07J1/00C07C15/18C07C49/784C07B59/00
CPCC07B59/001C07B59/007C07B2200/05C07C5/03C07C45/67C07J1/0059C07C15/18C07C49/784
Inventor 苏陈良邱春天李瑛
Owner SHENZHEN UNIV
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