Alpha,alpha-difluoroallyl aromatic hydrocarbon compound and preparation method thereof

A technology for difluoroallyl aromatic hydrocarbons and compounds, which is applied in the field of organic chemical synthesis, can solve the problem of less organic fluorides, achieve mild reaction conditions, eliminate pre-functionalization steps, and have broad application prospects

Inactive Publication Date: 2019-07-12
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] At present, there are very few studies on the use of transition metal-catalyzed C–H bond func

Method used

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  • Alpha,alpha-difluoroallyl aromatic hydrocarbon compound and preparation method thereof
  • Alpha,alpha-difluoroallyl aromatic hydrocarbon compound and preparation method thereof
  • Alpha,alpha-difluoroallyl aromatic hydrocarbon compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032](1) Under atmospheric atmosphere, mix 0.1mmol N-methoxy-4-methylbenzamide, 0.02mmol sodium acetate, 0.002mmol pentamethylcyclopentadienyl rhodium dichloride dimer and 0.12mmol 1-(5,5-difluoro-3-methyl-3,4-pentadienyl)benzene was sequentially added to a reaction flask filled with 0.5mL 1,2-dichloroethane to obtain a mixture;

[0033] (2) React the above mixture at room temperature (25-30° C.) for 12 h under stirring, and separate by silica gel column chromatography to obtain α,α-difluoroallyl aromatic hydrocarbon compound 1 containing all-carbon quaternary carbon centers.

Embodiment 2～46

[0035] Embodiments 2 to 46 are the same as Embodiment 1, except that:

[0036] Table 1 Examples 2-46

[0037]

[0038]

[0039]

Embodiment 47

[0041] This example is basically the same as Example 1, the difference is that in step (1), 0.1mmol N-methoxy-4-methylbenzamide, 0.2mmol sodium acetate, 0.02mmol pentamethylcyclopentadiene Alkenyl rhodium dichloride dimer and 1.2mmol 1-(5,5-difluoro-3-methyl-3,4-pentadienyl)benzene were sequentially added to 2mL 1,2-dichloroethyl The mixture was obtained in a reaction flask of alkane.

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PUM

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Abstract

The invention discloses an alpha,alpha-difluoroallyl aromatic hydrocarbon compound containing total carbon quaternary carbon center and a preparation method thereof. N-methoxy benzamide compound, sodium acetate, dichloropentamethyl cyclopentadienylrhodium(III) dimer and 1,1-difluoroallenes are sequentially added to a reaction flask containing a solvent, and then react under stirring at room temperature. After the reaction is completed, the alpha,alpha-difluoroallyl aromatic hydrocarbon compound containing total carbon quaternary carbon center is separated by silica gel column chromatography. As that preparation method of the invention has mild reaction condition, simple operation, raw materials adopted are low in cost, simple and easy to obtain, and tedious pre-functionalization steps areavoided, the substrate has wide application range. The alpha,alpha-difluoroallyl aromatic hydrocarbon compound prepared by the preparation method can be used as a class of novel alpha,alpha-difluoroolefin compounds containing total carbon quaternary carbon center with novel structures, and the difluoroolefin compounds have a broad application prospect in the research and development of drugs and materials.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to an α,α-difluoroallyl aromatic hydrocarbon compound containing an all-carbon quaternary carbon center and a preparation method thereof. Background technique [0002] Organic fluorides containing all-carbon quaternary carbon centers, as a special class of compounds containing all-carbon quaternary carbon centers, usually have unique physical and chemical properties and biological activities, and related research has great significance in the development of new functional materials, drug development and other fields. Wide range of applications. Therefore, the preparation of organic fluorides containing all-carbon quaternary carbon centers has always been one of the hot and difficult research areas in synthetic chemistry. [0003] At present, it is a relatively common strategy to prepare organic fluorides containing this structural unit by constructing...

Claims

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Application Information

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IPC IPC(8): C07C239/14C07C291/02C07C319/20C07C323/62C07J41/00C07D213/82C07F5/02C07F7/10
CPCC07C239/14C07C291/02C07C319/20C07C323/62C07J41/0072C07D213/82C07F5/025C07F7/10C07B2200/07
Inventor 冯超王成强
Owner NANJING UNIV OF TECH
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