Synthesis method of beta, beta-diaryl alkene

Abstract

The invention discloses a synthesis method of beta, beta-diaryl alkene, which comprises the following steps that: in an organic acid solvent, in the presence of a palladium catalyst and a silver salt, a halogenated aromatic hydrocarbon and an end alkenyl compound are subjected to a coupling reaction to obtain the beta, beta-diaryl alkene, wherein the organic acid solvent is acetic acid, the palladium catalyst is palladium acetate, the silver salt is silver acetate, silver carbonate or silver oxide, the halogenated aromatic hydrocarbon is iodo aromatic hydrocarbon, and the coupling reaction is operated at a reaction temperature of 80 to 130 DEG C for 0.25 to 24 hours. With the method, the environmentally friendly organic acid is used as the solvent, and the silver salt is used as an additive; and the method has the advantages of small amount of catalyst, mild reaction conditions, simple post-treatment, and high yield of a product, without adding other ligands and the like.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a synthesis method of β, β-diarylene. Background technique [0002] β,β-Diarylated alkenes are important intermediates in the synthesis of certain pharmaceuticals. Such as a cinnamic amides compound (Synthesis and α-Glucosidase Inhibitory Activity of Cinnamic Amides. Chin. J. Org. Chem. 2007, 27, 5 (in Chinese)) with α-glucosidase inhibitory activity, one of the compounds involved in its synthesis The important intermediate is β, β-diaryl propionate. In addition, in some other drug synthesis ((a) Diphenylpropionic acids as new AT(1) selective angiotensin II antagonists.J.Med.Chem.1996,39,2197.(b)Eur.Pat.EP 612,741, 1994.Chem.Abstr.1995,122,314547p.(c)US Pat.US 4,342,781,1982.Chem.Abstr.1982,97,215790w.), all related to this kind of β,β-diarylene intermediates. This kind of compound can be synthesized by conventional Witting reaction, but this method has many steps, an...

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Problems solved by technology

[0006] Although there are many reports about Heck coupling reactions carried out in protic solvents, most of them are water and co-solvents, such as N, N-dimethylformamide-water (Aqueous DMF-Potassium Carbonate as a Substitute for Thallium and Silver Additives in the Palladium-Catalyzed Conversion of Aryl Bromides to Acetyl Arenes.J.Org.Chem.2001,66:4340.), ethanol-water (Palladium(II)chloride / EDTA-catalyzed biaryl homo-coupling of aryl halides in aqueous medium in the presence of ascorbic acid. Tetrahedron Lett. 2006, 47 (43): 7625.) and other mixed solvents, there are also studies on the Heck reaction in pure water medium, but generally need to add some special additives, such as phase transfer catalyst , surfactants (Remarkably facile Heck and Suzuki reactions in water using a simple cationic surfactant and ligand-free palladium catalysts. Tetrahedron Lett. 2005, 46: 3557.), etc., which lead to certain limitations in the application of catalytic systems in organic synthesis , and the use of more acidic organic acid solvents such as HOAc as the solvent for this reaction has not been reported at present, because in the usual Heck reaction, the base is indispensable, and the organic acid can completely invalidate the base to react Difficult to happen

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