Method for catalyzing decarboxylation coupling reaction by 1,2,3-triazole monosubstituted 1,3,5-s-triazine compound coordinated with CuSO4.5H2O

A catalytic decarboxylation, cuso4·5h2o technology, applied in the direction of organic compound/hydride/coordination complex catalysts, preparation of organic compounds, hydrocarbons, etc., can solve environmental pollution, difficult to handle acetylene gas, harsh reaction conditions and other issues, to achieve the effects of reducing environmental pollution, good substrate applicability, and short reaction time

Inactive Publication Date: 2015-12-09
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these reactions usually have many disadvantages: 1. Metal reagents need to be prepared in advance; 2. These metal reagents are sensitive to water and air; 3. Metal reagents require multifunctional compatibility; 4. Acetylene gas is difficult to handle as an alkyne source; Methylsilylacetylene will produce an equivalent amount of organic waste after the reaction; 6. The introduced bis(tributyltin)acetylene needs a strong base to deprotect
However, it cannot

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Under nitrogen protection, mix 0.1206g (0.5mmol) p-methoxy iodobenzene with 0.0870g (0.5mmol) phenylpropylic acid, 0.0125g (0.05mmol) CuSO 4 ·5H 2 O, 0.1382g (1.0mmol)K 2 CO 3 , 0.0142g (0.05mmol) 2,4-dimethoxy-6-(4-phenyl-1-hydrogen-1,2,3-triazolyl)-1,3,5-s-triazine was added to 3mLN , in N-dimethylformamide, stirred and mixed evenly, heated to 130°C, reacted at constant temperature for 12 hours, cooled to room temperature, extracted with ethyl acetate, and separated the product by column chromatography to obtain 1-methoxy-4-(benzene Ethynyl) benzene, its yield is 93%.

Embodiment 2

[0019] In Example 1, the p-methoxy iodobenzene used is replaced with equimolar o-methyl iodobenzene, and other steps are the same as in Example 1 to prepare 1-methoxy-2-(phenylethynyl) benzene, The yield thereof was 86%.

Embodiment 3

[0021] In Example 1, the p-methoxy iodobenzene used was replaced by equimolar iodobenzene, and the other steps were the same as in Example 1 to prepare 1,2-tolanine with a yield of 95%.

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Abstract

The invention discloses a method for catalyzing decarboxylation coupling reaction by a 1,2,3-triazole monosubstituted 1,3,5-s-triazine compound coordinated with CuSO4.5H2O. By taking CuSO4.5H2O which is good in stability and cheap and easily available and the triazine compound which is stable in water and air and high in functionalization as a catalytic system, the method catalyzes decarboxylation coupling reaction on aryl halide and phenylpropiolic acid. The reaction system is free of a conventional phosphine ligand, so that the environmental pollution is reduced, and the method has good substrate applicability. The target product is easy to separate and purify and high in yield. The method disclosed by the invention is an efficient and safe decarboxylation coupling reaction system and can be applied to constructing Csp-CsP2 bonds.

Description

technical field [0001] The invention belongs to the technical field of decarboxylation coupling reaction, and specifically relates to a 1,2,3-triazole monosubstituted 1,3,5-s-triazine compound synergized with CuSO 4 ·5H 2 O catalyzed decarboxylation coupling reaction method. Background technique [0002] Alkynes are an important class of species for efficient construction of organic synthesis units. At present, transition metal-catalyzed coupling reactions are the main method for synthesizing alkynes, and common reactions include classic organic reactions such as Negishi, Stille, and Sonogashira. However, these reactions usually have many disadvantages: 1. Metal reagents need to be prepared in advance; 2. These metal reagents are sensitive to water and air; 3. Metal reagents require multifunctional compatibility; 4. Acetylene gas is difficult to handle as an alkyne source; Methylsilylacetylene will produce an equivalent amount of organic waste after the reaction; 6. The i...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C1/32C07C15/54C07C41/30C07C43/215C07C201/12C07C205/06B01J31/22
Inventor 高子伟王振华王秀孙华明张伟强张国防杨丹
Owner SHAANXI NORMAL UNIV
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