4,4-dialkylthio-1-phenyl-3-buten-1-one derivatives and synthesis method thereof

A synthesis method and technology of dithioketal are applied in the field of 4,4-dialkylthio-1-phenyl-3-butene-1-one derivatives and synthesis, and can solve internal olefin alkylation reaction There are few reports and no reports of alkylation reactions, etc., to achieve the effects of a wide range of substrates, diverse preparations, and high atom economy.

Active Publication Date: 2019-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Before 2008, there were very limited reports on the application of visible light catalysis in the field of organic synthesis
Although visible light-catalyzed alkylation of terminal olefins has been reported, there are few reports on the alkylation of internal olefins
A

Method used

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  • 4,4-dialkylthio-1-phenyl-3-buten-1-one derivatives and synthesis method thereof
  • 4,4-dialkylthio-1-phenyl-3-buten-1-one derivatives and synthesis method thereof
  • 4,4-dialkylthio-1-phenyl-3-buten-1-one derivatives and synthesis method thereof

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Embodiment 1

[0029]

[0030] The specific process is: weigh dithioketene 2a (67mg, 0.3mmol), Ru(bpy) in the glove box 3 Cl 2 (4mg, 0.006mmol), sodium carbonate (25mg, 0.3mmol), α-bromoacetophenone 3a (119mg, 0.6mmol), was added to a 25mL tube with a branch, and acetonitrile (3mL) was added under nitrogen atmosphere Under the irradiation of 26W white CFL lamp, react at room temperature for 24h. After the reaction was complete, the solvent was removed by rotary evaporation under reduced pressure, followed by column chromatography (petroleum ether (60-90°C) / ethyl acetate: 10:1, v / v) to obtain a light yellow liquid product 1a (72 mg, yield 70 %). The target product was confirmed by NMR spectroscopy.

[0031]

[0032] The specific process is: weigh 1a (68mg, 0.2mmol), NH 2 NH 2 ·H 2 O (120uL, 2.0mmol, 85%) was added to a 25mL sealed tube, 2mL of toluene was added, and the mixture was placed in an oil bath at 120°C for 12h. After the reaction was complete, cool to room temperature, ...

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Abstract

The invention discloses 4,4-dialkylthio-1-phenyl-3-buten-1-one derivatives and a synthesis method thereof. Dithioketene acetal which is easy to prepare, which has structural diversity and multiple reaction centers, and which is adopted as a raw material and alpha-bromoacetophenone are subjected to a coupling reaction under the action of a ruthenium complex and illumination to synthesize a series of 4,4-dialkylthio-1-phenyl-3-buten-1-one derivatives with different structures. The derivatives can be further converted into functional products. The method has the advantages of easily available rawmaterials, simple operation, mild reaction conditions, and diversified functional groups.

Description

technical field [0001] The invention relates to a method for preparing four-substituted olefin compound 4,4-dioxylthio-1-phenyl-3-buten-1-one derivatives by catalyzing visible light. The C(sp 2 )-C(sp 3 ) bond coupling reaction to prepare 4,4-dialkylthio-1-phenyl-3-butene-1-one derivatives. Compared with the existing synthetic methods of multi-substituted olefin derivatives, the present invention has easy-to-obtain raw materials, simple operation, mild reaction conditions, and environmental friendliness; and utilizes light energy to realize the conversion of organic matter without adding any oxidizing agent or reducing agent, and has the advantages of Features high atom economy. Background technique [0002] Visible light is an inexpensive and abundant natural resource. Therefore, how to efficiently use visible light to realize the conversion of organic compounds is widely favored by chemists. Before 2008, there were very limited reports on the application of visible li...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/22C07D231/18
CPCY02B20/00
Inventor 余正坤汪全南
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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