Preparation method of trifluorostyrene compound

Abstract

The invention provides a synthesis method of a trifluorostyrene compound. According to the method provided by the invention, the trifluorostyrene compound can be synthesized from an accessible fluorin containing raw material and various substituted arylboronic acid compounds in an alkali condition by using a phosphine ligand or a multiphosphine ligand and using bis(dibenzylideneacetone)dipalladium as a catalyst. By adopting the method provided by the invention, the fluorine spectrum yield is extremely improved, while the use amount of the catalyst is obviously reduced.

Description

technical field [0001] The invention relates to the field of synthesis; in particular, the invention relates to a new synthesis method of trifluorostyrene compounds. Background technique [0002] Fossil energy resources are currently the main source of energy. However, the proven reserves of oil and coal indicate that in view of the current world consumption rate, it is imperative to find alternative new green and clean energy sources. One of the main purposes of my country's national energy reserves and new energy development. [0003] Hydrogen energy has the advantages of cleanliness and inexhaustibility, and may become an important secondary energy source in the energy arena of the 21st century. Proton exchange membrane fuel cell is a kind of fuel cell that generates electricity and heat by the action of hydrogen-containing fuel and air. It has the characteristics of relatively low temperature and normal pressure, plus it has no chemical hazards to the human body and is h...

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Problems solved by technology

However, many synthetic methods of trifluorostyrene compounds reported in the prior art have many reaction steps or need to use highly toxic drugs (such as SbF 5 ), or low yield, or complex operation, or low reaction selectivity and other defects

[0005] In 1988, Heinze and Burton reported that a kind of trifluoroethylene base metal reagent was prepared as raw material with trifluoroethylene bromide or trifluorobromoethylene, and then palladium catalyzed coupling generated the reaction of trifluorostyrene, and the productive rate was higher (J.Org .Chem.1988,53,2714), but the method is complicated to operate and trifluoroiodoethylene or trifluorobromoethylene are expensive reagents

[0006] WO 03051801 reported a coupling reaction of 1,2,2-trifluorozinc reagent prepared from HFC-134a and aryl halide under palladium catalysis, although the yield of trifluorostyrene obtained by this method is relatively high, But there are many steps, need to react at low temperature, use the low butyllithium of safety and unfriendly HFC-134a to the environment, the catalyst consumption height (calculated as zinc chloride is about 1.5mol% or higher; According to iodobenzene Calculated, the dosage is about 1.9mol%) and many other disadvantages

[0007] In 2011, Ogoshi reported on JACS (J.Am.Chem.Soc.2011,133,3256) that the method for coupling tetrafluoroethylene with diphenylzinc reagent was used to generate trifluorostyrene. Dangerous tetrafluoroethylene and expensive diphenylzinc reagents are used

[0008] Chinese patent application CN 102241554 discloses a method for synthesizing trifluorostyrene, but the operation of the method is relatively complicated and the amount of catalyst used is relatively high

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