Process for the preparation of aromatic alkenyl compounds

Abstract

The invention discloses a preparation method of an aromatic alkenyl compound. The aromatic alkenyl compound comprises thioether and a carbon-carbon double bond substrate, wherein the ratio of the amount of substance of the thioether and the carbon-carbon double bond substrate is 1:(2 to 4); the compound further comprises [Cp*IrCl2]2 and Cu(OAc)2, wherein the ratio of the amount of substance of the[Cp*IrCl2]2 and the thioether is (0.005 to 0.05):1, and the ratio of the amount of substance of the Cu(OAc)2 and the thioether is (1.2 to 2.4):1; the thioether, the carbon-carbon double bond substrate, the [Cp*IrCl2]2 and the Cu(OAc)2 are mixed, and are stirred in solvent for 12 h, and the reaction temperature is 60 to 90 DEG C. The preparation method disclosed by the invention has the advantagesthat the time consumption of a reaction is short; the selectable range of the thioether and the carbon-carbon double bond substrate is wide; the reaction does not need to be performed under oxygen-free and high-pressure conditions; the reaction conditions are mild; the catalyst consumption is less; the method is applied to industrial production; the production cost is saved; the production cycleis shortened; good economy is realized; the controlled synthesis of target products is realized; the controllability is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of an aromatic alkenyl compound. Background technique [0002] Traditional transition metal-catalyzed cross-coupling reactions provide an efficient method for the synthesis of carbon-carbon and carbon-heterobond bonds. Many classic coupling reactions are more and more widely used, but they still have disadvantages that cannot be ignored: this type of reaction needs to pre-functionalize the substrate in advance to make electrophiles such as halides or halide-like compounds and hydrophilic reagents. Nuclear reagents, etc. The steps of the reaction are increased and the atom economy is reduced. Therefore, whether the functional group of the carbon-hydrogen bond can be directly realized, so that the substrate can directly participate in the reaction, will greatly improve the efficiency. [0003] Due to the step and atom economy, the most commonly used strategy...

AI Technical Summary

Problems solved by technology

Many classic coupling reactions are more and more widely used, but they still have disadvantages that cannot be ignored: this type of reaction needs to pre-functionalize the substrate in advance to make electrophiles such as halides or halide-like compounds and hydrophilic reagents. Nuclear reagents, etc.

The common problems of the above synthesis techniques are: the reaction temperature is higher than 120°C, the reaction yield is low, the amount of catalyst required is high, some of them need to be carried out under the condition of anaerobic and high pressure, and the selectivity of the reaction is poor.

So far, iridium-catalyzed thioether-directed C–H alkenylation reactions have not been reported

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