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A kind of method of iron catalysis oxyalkylene synthesis ketone
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A technology of alkylene oxide and catalyst, which is applied in the direction of chemical instruments and methods, preparation of organic compounds, steroids, etc., can solve the problems of difficulty in removing residual palladium, high reaction cost, etc., and achieve cheap oxidants, high selectivity, and high yield Effect
Active Publication Date: 2020-06-12
NANJING NORMAL UNIVERSITY
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Problems solved by technology
[0003] The technical problem solved: the purpose of the present invention is to solve the technical problem that existing Wacker oxidation reaction needs expensive palladium catalyst and copper as pro-oxidant to cause high reaction cost, and it is difficult to remove residual palladium in the pharmaceutical industry, and provides a kind of iron catalytic oxidation A method for synthesizing ketones from alkenes, which has the characteristics of wide source of catalyst, low cost and environmental protection; cheap oxidant and no waste; wide and stable source of substrate; mild reaction conditions, good selectivity and high yield; substrate functional group phase Good compatibility; complex alkenes can efficiently synthesize corresponding ketones
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Embodiment 1
[0029] Synthesis of Compound 1
[0030] In the air, ferrous chloride (0.05 mmol), alkene 1a (0.5 mmol), triethylsilane (1.5 mmol) and ethanol (2.0 mL) were sequentially added to a 25 mL reaction flask. After mixing uniformly at room temperature, the reaction mixture was reacted at room temperature for 6 h. After the reaction was completed, ammonia water (0.5 mL) was added and stirred for 1 h. Then, 5 mL of water was added, and the mixture was extracted with ether (5 mL×3). The organic phases were combined, and the solvent was evaporated under reduced pressure, and then the solvent was evaporated under reduced pressure, and the yield was 98% by column chromatography.
Embodiment 2
[0032] Synthesis of Compound 2
[0033]In the air, ferrous trichloride (0.05 mmol), alkene 1b (0.5 mmol), triethoxysilane (1.5 mmol) and methanol (2.0 mL) were sequentially added to a 25 mL reaction flask. After mixing uniformly at room temperature, the reaction mixture was reacted under reflux for 24 h. After the reaction was completed, ammonia water (0.5 mL) was added and stirred for 1 h. Then, 5 mL of water was added, and extracted with ether (5 mL×3), the organic phases were combined, and the solvent was evaporated under reduced pressure, and then the solvent was evaporated under reduced pressure, and the yield was 92%.
Embodiment 3
[0035] Synthesis of Compound 3
[0036] In the air, ferrous trifluoromethanesulfonate (0.05 mmol), alkene 1c (0.5 mmol), dimethylethoxysilane (1.5 mmol) and tert-butanol (2.0 mL) were sequentially added to a 25 mL reaction flask. After mixing uniformly at room temperature, the reaction mixture was reacted under reflux for 9 h. After the reaction was completed, ammonia water (0.5 mL) was added and stirred for 1 h. Then, 5 mL of water was added, extracted with ether (5 mL×3), the organic phases were combined, the solvent was evaporated under reduced pressure, and the solvent was evaporated under reduced pressure to obtain a yield of 89% by column chromatography.
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Abstract
The invention discloses a method for synthesizing ketoneby oxidation of alkene under catalysis of iron, and belongs to the field of catalyzed synthesis technologies and fine chemical synthesis. According to the specific method, air or oxygen is taken as an oxidizing agent under the acceleration action ofhydrosilaneand a ketone compound is synthesized byoxidation of alkene under catalysis of iron. The method has the advantages that the catalyst is wide in source, cheap and environment-friendly; the oxidant is wide in source and cheap and does not generate a waste; the reaction conditions are mild, the selectivity is high and the yield is high;a substrate is wide and stable; a functional group of the substrate is good in compatibility and the application range of the substrate is wide; and alkene molecules can be well converted into the ketone. The separation yield of a target product reaches 98% under the optimized reaction conditions.
Description
technical field [0001] The invention belongs to the field of catalytic synthesis technology and fine chemical synthesis, and more particularly relates to an iron catalysis method that can be used for the oxidation of complex alkenes to ketones, which is a method for preparing ketones by oxidizing alkenes with iron catalyzed air or oxygen. Background technique [0002] The structural unit of ketone is widely present in organic compounds, and at the same time, it is a very important transformation functional group, which is used in the synthesis of medicines, pesticides, natural products, organic materials, etc. Therefore, the invention of a universal, efficient, safe and economical method for synthesizing ketones has important research significance and application value. The most famous method for synthesizing ketones is the Wacker oxidation reaction, which requires palladium as a catalyst, copper salt as a co-oxidant and air as an oxidant, so that the reaction can proceed sm...
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