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A Novel Catalytic Direct Dehydrogenation Coupling Method for the Synthesis of Thiophene-Containing Alkanes

A technology for dehydrogenation coupling and compounds, applied in the direction of organic chemistry, etc.

Active Publication Date: 2020-10-30
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Recently, many cheap metals have been used in catalytic reactions, including copper, iron, nickel, etc., but it is still a great challenge to select a new cheap and efficient transition metal catalyst.

Method used

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  • A Novel Catalytic Direct Dehydrogenation Coupling Method for the Synthesis of Thiophene-Containing Alkanes
  • A Novel Catalytic Direct Dehydrogenation Coupling Method for the Synthesis of Thiophene-Containing Alkanes

Examples

Experimental program
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Effect test

preparation example 1

[0026] Add N-8-quinoline pivalamide (0.2mmol), nickel bromide (0.04mmol), 2,4,6-trimethylbenzoic acid (0.08mmol), potassium dihydrogen phosphate (0.4 mmol), thiophene (0.6mmol), silver carbonate (0.6mmol), tetrabutylammonium bromide (0.6mmol), DMSO (0.5ml) was added under nitrogen, and reacted at 160°C for 24h. After the reaction was completed, it was lowered to room temperature, 20ml of distilled water was added, extracted with ethyl acetate (3x10ml), dried by adding anhydrous sodium sulfate, and the product was separated by column chromatography with a yield of 64%.

preparation example 2

[0028] Add N-8-quinoline pivalamide (0.2mmol), nickel bromide (0.04mmol), 2,4,6-trimethylbenzoic acid (0.08mmol), potassium dihydrogen phosphate (0.4 mmol), 2-chlorothiophene (0.6mmol), silver carbonate (0.6mmol), tetrabutylammonium iodide (0.6mmol), DMF (0.5ml) was added under nitrogen, and reacted at 160°C for 24h. After the reaction was completed, it was lowered to room temperature, 20ml of distilled water was added, extracted with ethyl acetate (3 x 10ml), dried by adding anhydrous sodium sulfate, and the product was separated by column chromatography with a yield of 63%.

preparation example 3

[0030] Add N-8-quinoline pivalamide (0.2mmol), nickel bromide (0.04mmol), 2,4,6-trimethylbenzoic acid (0.08mmol), potassium dihydrogen phosphate (0.4 mmol), 2-bromothiophene (0.6mmol), silver carbonate (0.6mmol), tetrabutylammonium iodide (0.6mmol), DMF (0.5ml) was added under nitrogen, and reacted at 160°C for 24h. After the reaction was completed, it was lowered to room temperature, 20ml of distilled water was added, extracted with ethyl acetate (3 x 10ml), dried by adding anhydrous sodium sulfate, and the product was separated by column chromatography with a yield of 61%.

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Abstract

The invention provides a novel catalytic direct dehydrogenation coupling method for synthesis of a thiophene structure-containing alkane compound. According to the method, based on a one-pot process, in the presence of a metal nickel salt as a catalyst, non-functional thiophene compounds containing different functional groups and fatty acid amide containing a positioning group as raw materials, an organic acid as a ligand, a high boiling point polar solvent, an inorganic salt as a base, a silver salt as an oxidizing agent and a phase transfer catalyst undergo a reaction at a temperature of 160 DEG C for 24h to produce a desired compound. Compared with the existing halogenation or lithium salt functionalization method, the method provided by the invention is free of thiophene compound pre-functionalization, greatly reduces intermediate steps, reduces a raw material cost and wastes produced in the reaction and has the characteristics of atom economy and high efficiency.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, and in particular relates to a novel catalytic direct dehydrogenation coupling method for synthesizing alkane compounds containing thiophene structure. 【Background technique】 [0002] As a ubiquitous substance in biologically active natural products and medicines, thiophene structure compounds can be directly used in organic synthesis and material research and development, especially in the fields of optoelectronic materials and pharmaceuticals. However, in the current preparation process, the cross-coupling reaction between the pre-functionalized thiophene reagent and the metallated or halogenated aromatic reagent is mainly used, and the pre-functionalized thiophene mainly exists in the halogenated or lithium-salted form. Therefore, in the synthesis process, the waste generated from the preparation of raw materials has become an environmental problem that needs to be solved urgently....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/12C07D409/14
CPCC07D409/12C07D409/14
Inventor 邱仁华王勰刘婷
Owner HUNAN UNIV
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