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Preparation method of symmetric 1,4-disubstituted-1,3-diacetylene

A disubstituted, diacetylene technology, applied in the field of chemical synthesis, can solve the problems of high price, large environmental pollution, complicated operation, etc., and achieve the effect of high practicability and selectivity

Inactive Publication Date: 2015-06-17
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reagents used, such as trimethylsilyne and palladium phosphine complexes, are expensive and highly toxic, and most of the reactions require several auxiliary reagents, the reaction cost is high, the operation is cumbersome and the post-processing is complicated and the environment is polluted.
[0004] With the development of transition metal catalytic reaction research, stoichiometric silver is often used as a promoter to improve the reactivity of metal ions (such as palladium, ruthenium, rhodium, etc.), but the application of silver compounds themselves as catalysts is very limited.
However, there has been no research on silver-catalyzed self-oxidative coupling of terminal alkynes.

Method used

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  • Preparation method of symmetric 1,4-disubstituted-1,3-diacetylene
  • Preparation method of symmetric 1,4-disubstituted-1,3-diacetylene
  • Preparation method of symmetric 1,4-disubstituted-1,3-diacetylene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 1 mmol of p-methoxyphenylacetylene, 0.01 mmol of silver nitrate and 0.5 mmol of sodium carbonate into a round bottom flask filled with 1 ml of acetonitrile, and stir for 2 hours at 50°C. After the reaction was completed, the solid was filtered out, and the solvent was spin-dried, and the product was obtained by column separation with a yield of 94%.

[0027]

[0028] 1 H NMR (400MHz, CDCl 3 , TMS) δ7.46(d, J=8.4Hz, 4H), 6.85(d, J=8.8Hz, 4H), 3.81(s, 6H). 13 C NMR (100MHz, CDCl 3 ): δ160.3, 134.1, 114.2, 113.8, 81.3, 72.8, 55.3. HRMS calcd for C 18 h 10 o 2 : 262.0994, found: 262.0997.

Embodiment 2

[0030] Add 1mmol of p-acetylphenylacetylene, 0.01mmol of silver nitrate and 0.5mmol of sodium carbonate into a round bottom flask containing 1ml of acetonitrile, and stir for 2 hours at 50°C. After the reaction was completed, the solid was filtered out, and the solvent was spin-dried, and the product was obtained by column separation, with a yield of 90%.

[0031]

[0032] 1 H NMR (CDCl 3 , 400MHz) δ7.94(d, J=8.4Hz, 4H) 7.62(d, J=8.4Hz, 4H), 2.62(s, 6H). 13 C NMR (100MHz, CDCl 3 ): δ196.7, 137.1, 132.7, 128.3, 126.0, 81.9, 76.6, 26.6. HRMS calcd for C 20 h 14 o 2 :286.0994.found: 286.0993.

Embodiment 3

[0034] Add 1mmol of 1-naphthyneacetylene, 0.01mmol of silver nitrate and 0.5mmol of sodium carbonate into a round bottom flask filled with 1ml of acetonitrile, and stir at 50°C for 2 hours. After the reaction was completed, the solid was filtered out, and the solvent was spin-dried, and the product was obtained by column separation with a yield of 89%.

[0035]

[0036] 1 H NMR (CDCl 3 , 400MHz) δ8.44(d, J=8.0Hz, 2H), 7.82-7.92(m, 6H), 7.43-7.68(m, 6H). 13 C NMR (100MHz, CDCl 3 ): δ133.9, 133.0, 132.1, 129.6, 128.3, 127.2, 126.6, 126.1, 125.1, 119.5, 81.0, 78.8. HRMS calcd for C 24 h 14 : 302.11096, found: 302.1092.

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Abstract

The invention discloses a preparation method of symmetric 1,4-disubstituted-1,3-diacetylene. Homocoupling of alkyne is carried out in a solvent in the presence of an alkali with silver as a catalyst to obtain the symmetric 1,4-disubstituted-1,3-diacetylene. The method has the advantages of simple operation, obtaining of corresponding diacetylene compounds at room temperature without air isolation or addition of a phosphine ligand or a precious metal, simple post-treatment, and very good practicality and economic values.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a method for preparing symmetrical 1,4-disubstituted-1,3-butadiynes from alkynes catalyzed by silver. Background technique [0002] 1,4-disubstituted-1,3-butadiyne is a kind of compound with special structure. From the perspective of spatial structure, it contains four sp hybridized carbon atoms, the four carbon atoms are arranged in a linear manner, and the overall structure presents a certain degree of rigidity; a conjugated structure can be formed between two triple bonds, so it is also called Conjugated diynes. Conjugated diynes themselves exist in many natural compounds, and their structures are common in natural products, antifungal drugs, and can also be used as the precursor of some dyes; they are often used in organic synthesis as a universal module for building molecules. Among them, conjugated diyne can be used as the equivalent of many functional groups; its rigid and...

Claims

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Application Information

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IPC IPC(8): C07B37/04C07C43/215C07C41/30C07C49/796C07C45/68C07C15/58C07C2/84C07D213/127C07C13/28
Inventor 朱余玲
Owner SHAOXING UNIVERSITY
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