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Preparation method of dialkyl sulfone compounds

A technology of dialkyl sulfone and salt compounds, which is applied in the field of preparation of dialkyl sulfone compounds, can solve problems such as difficulty in applying target products, and achieve good guiding significance and application prospects

Active Publication Date: 2020-01-31
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in the synthesis methods of various sulfone compounds, the synthesis of dialkyl sulfone compounds still has certain limitations, and the existing synthesis methods are difficult to apply to various target products with different alkyl substitutions.

Method used

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  • Preparation method of dialkyl sulfone compounds
  • Preparation method of dialkyl sulfone compounds
  • Preparation method of dialkyl sulfone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Add 0.2mmol of N-cyclohexyl-2,4,6-triphenylpyridine tetrafluoroborate, 0.4mmol of potassium metabisulfite, 0.003mmol (1.5mol%) of iridium photosensitizer Ir[ dF(CF 3 )ppy] 2 (bpy)PF 6, stop the reaction tube with a stopper and place it in high-purity nitrogen to replace the gas, so that the system is in anhydrous and oxygen-free conditions, and then add 2.5mL of dry dimethyl sulfoxide and 0.6mmol of 1-phenyl-1-triisopropyl Siloxyethylene, placed in a visible light reaction device and stirred until completely reacted. After the reaction was monitored by TCL, pour the reaction liquid into 50 mL of water, extract three times with 20 mL of ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and use a mixture of petroleum ether and ethyl acetate as the mobile phase The corresponding 2-(cyclohexylsulfonyl)-1-phenyl-1-ethanone (2-(Cyclohexylsulfonyl)-1-phenylethan-1-one) example 1 can be obtained by c...

Embodiment 2

[0034]

[0035] Add 0.2mmol of N-cyclohexyl-2,4,6-triphenylpyridine tetrafluoroborate, 0.25mmol of potassium metabisulfite, 0.002mmol (1.5mol%) of iridium photosensitizer Ir[ dF(CF 3 )ppy] 2 (bpy)PF 6 , stop the reaction tube with a stopper and place it in high-purity argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 2.5 mL of dry dimethyl sulfoxide and 0.4 mmol of 1-(4-methylphenyl) -1-Triisopropylsiloxyethylene, placed in a visible light reaction device and stirred until complete reaction. After the reaction was monitored by TCL, the reaction liquid was poured into 50 mL of water, extracted three times with 20 mL of ether, the combined organic phases were dried with anhydrous sodium sulfate, concentrated under reduced pressure, and a mixture of petroleum ether and ethyl acetate was used as the mobile phase for column extraction. Chromatographic separation, the corresponding 2-(cyclohexylsulfonyl)-1-(4-methylphenyl)-1-etha...

Embodiment 3

[0038]

[0039] Add 0.2 mmol of N-cyclohexyl-2,4,6-triphenylpyridine tetrafluoroborate, 0.45 mmol of potassium metabisulfite, 0.004 mmol (1.5 mol%) of iridium photosensitizer Ir to the dry test tube[ dF(CF 3 )ppy] 2 (bpy)PF 6 , stop the reaction tube with a stopper and place it in high-purity nitrogen to replace the gas, so that the system is in anhydrous and oxygen-free conditions, and then add 2.5 mL of dry dimethyl sulfoxide and 0.7 mmol of 1-(4-trifluoromethylphenyl )-1-triisopropylsiloxyethylene, placed in a visible light reaction device and stirred until complete reaction. After the reaction was monitored by TCL, pour the reaction liquid into 50 mL of water, extract three times with 20 mL of ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and use a mixture of petroleum ether and ethyl acetate as the mobile phase Carry out column chromatography separation, can obtain corresponding 2-(cyclohexylsulfony...

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of dialkyl sulfone compounds. The preparation method comprises following steps: under catalysis of visible light, various simple or complex alkyl substituted N-alkyl pyridinium salts and a photocatalyst are adopted to generate alkyl free radicals, sulfonyl free radicals are obtainedthrough cascade reaction with sulfur dioxide, and silyl enol ether is attacked, so that a series of dialkyl sulfone compounds are efficiently constructed. According to the method, the dialkyl sulfonecompounds can be efficiently, simply and conveniently synthesized, sulfonyl-derived potassium metabisulfite required by the reaction is a cheap and easily available chemical raw material, the use of strongly acidic sulfonic acid and sulfonyl chloride in the traditional sulfonyl compound synthesis is avoided, and the method has the advantage of large-scale industrial preparation.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of dialkyl sulfone compounds. Background technique [0002] Over the past few years, strategies to use photoreactions to catalyze organic transformations have developed rapidly (T.P. Yoon, M.A. Ischay, J.Du, Nat. Chem. 2010, 2, 527; J.M.R. Narayanam, C.R.J. Stephenson, Chem. Soc. Rev. 2011 , 40, 102; J.Xuan, W.-J.Xiao, Angew.Chem.Int.Ed.2012, 51, 6828; L.Shi, W.-J.Xia, Chem.Soc.Rev.2012, 41, 7687 ; C.K. Prier, D.A. Rankic, D.W.C. MacMillan, Chem. Rev. 2013, 113, 5322; D.M. Schultz, T.P. Yoon, Science. 2014, 343, 985). In most cases, photocatalytic processes require one-electron transfer from excited-state photocatalysts to substrates to generate free radical species as reaction intermediates. At present, in this research field, iridium complex photocatalysts are widely used due to their advantages of small dosage, high efficiency and w...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/24C07D333/22C07D335/02
CPCC07C315/00C07D333/22C07D335/02C07C317/24
Inventor 叶盛青吴劼王雪枫
Owner TAIZHOU UNIV
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