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Methods for the synthesis of organic sulfides by using sulfides and organic sulfur-indium complexes

A technology of organic sulfur and complexes, applied in the field of synthesis of carbon-sulfur bonds, which can solve problems such as long reaction time and excess catalyst

Inactive Publication Date: 2010-08-18
KNU IND COOPERATION FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction requires an excess of catalyst and a long reaction time

Method used

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  • Methods for the synthesis of organic sulfides by using sulfides and organic sulfur-indium complexes
  • Methods for the synthesis of organic sulfides by using sulfides and organic sulfur-indium complexes
  • Methods for the synthesis of organic sulfides by using sulfides and organic sulfur-indium complexes

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Experimental program
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Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of 2-phenyl naphthyl sulfide

[0045] Formula 5

[0046]

[0047] A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 mL) was stirred for 5 minutes under nitrogen atmosphere. To this solution was added 2-bromonaphthalene (103.5 mg, 0.5 mmol) dissolved in 0.5 mL of DMF, and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added In(SPh) in DMF (1 mL) 3 (74mg, 0.167mmol) and diisopropylethylamine (65mg, 0.5mmol). The reaction mixture was stirred at 100°C for 2 hours. The solution was cooled to room temperature, and 1 mL of hydrochloric acid (5% aqueous solution) was added thereto to terminate the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times), and washed successively with 10 mL of water, saturated NaHCO 3 solution (10 mL) and saturated NaCl solution (20 mL). Extract organic compounds with anhydrous MgSO 4 Dry and filter. Af...

Embodiment 2

[0049] Embodiment 2: the preparation of ethyl 3-isopropylthiobenzoate

[0050] Formula 6

[0051]

[0052] A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 mL) was stirred for 5 minutes under nitrogen atmosphere. To this solution was added ethyl 3-bromobenzoate (114.5 mg, 0.5 mmol) dissolved in 0.5 mL of DMF, and the reaction mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added In(SPr i ) 3 (57mg, 0.168mmol) and diisopropylethylamine (65mg, 0.5mmol). The reaction mixture was stirred at 100°C for 2 hours. The solution was cooled to room temperature, and 1 mL of hydrochloric acid (5% aqueous solution) was added thereto to terminate the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times), and washed successively with 10 mL of water, saturated NaHCO 3 solution (10 mL) and saturated NaCl solution (20 mL). Extract the organic compounds with anhydrous MgSO 4 Dry a...

Embodiment 3

[0054] Embodiment 3: Preparation of 1-phenylnaphthyl sulfide

[0055] Formula 7

[0056]

[0057] A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 mL) was stirred for 5 minutes under nitrogen atmosphere. To this solution was added 1-naphthalene triflate (138.1 mg, 0.5 mmol) dissolved in DMF (0.5 mL), and the reaction mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added In(SPh) in DMF (1 mL) 3 (74mg, 0.167mmol)) and diisopropylethylamine (65mg, 0.5mmol). The reaction mixture was maintained at 100°C for 2 hours. The solution was cooled to room temperature, and 1 mL of hydrochloric acid (5% aqueous solution) was added thereto to terminate the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times), and washed successively with 10 mL of water, saturated NaHCO 3 solution (10 mL) and saturated NaCl solution (20 mL). Extract the organic compounds with anhydrous MgSO 4 ...

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Abstract

The present invention relates to a novel synthesis method for the formation of carbon- sulfur bonds by the reaction of an organic sulfur-indium complex with nucleophile in the presence of a palladium catalyst. The present invention provides a synthesis method to prepare several kinds of organic sulfides which are difficult to be prepared by the conventional synthesis methods. A short reaction time and quantitative yield are the advantages of this method. In addition, several kinds of organic sulfide can be prepared by the selection of nucleophile and organic sulfur-indium complex to be used.

Description

technical field [0001] The invention relates to a method for synthesizing organic sulfur compounds by reacting sulfides with organic sulfur indium complexes. More specifically, the traditional synthetic method for forming carbon-sulfur bonds is achieved through the reaction between nucleophiles and electrophiles in the presence of transition metal catalysts. Organic halides act as electrophiles and thiols act as nucleophiles. Thiolate ions were used instead of thiols as nucleophiles because thiolate ions are more nucleophilic than thiols. And this traditional synthetic method needs high reaction temperature and long reaction time. It is therefore an object of the present invention to provide a novel reagent to increase the nucleophilicity of thiols and to obtain high yields of organosulfur compounds in relatively short reaction times. The synthesis method of the present invention is useful for the preparation of organosulfur compounds whose synthesis method has not been rep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C321/02
CPCC07C319/14C07C321/30C07C321/20C07C323/61C07C323/62C07C319/26C07C319/28C07C319/30
Inventor 李弼镐
Owner KNU IND COOPERATION FOUND
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