Preparation method of Alpha-naphthyl containing diarylketone compound

Abstract

The invention belongs to the technical field of pharmaceutical chemical intermediates and related chemistry and provides a preparation method of Alpha-naphthyl containing diarylketone compound; the preparation method comprises: reacting, under the action of a metal catalyst, a ligand and an alkali, 1-(chloromethyl)naphthalene and its derivatives as materials with phenylacetonitrile compounds in an anhydrous organic solvent, and converting, under the action of an oxidant, into the Alpha-naphthyl containing diarylketone compound. The preparation method has the advantages that the synthetic route is short, the conditions are mild, operating is simple, it is probable to industrialize the method, the yield of diarylketone products is high, it is possible, on naphthalene rings of the diarylketone compound synthesized by using the method, to further functionalize methyl so that the functional molecules, such as drug intermediates, optical materials, are acquired.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a preparation method of an α-naphthyl diaryl ketone compound. Background technique [0002] Diaryl ketone structures are ubiquitous in biologically active molecules. At the same time, diaryl ketone compounds are also important intermediates for the synthesis of natural products and organic functional materials. Therefore, it is of great significance and application value to develop efficient and highly selective methods for synthesizing diaryl ketones. At present, there are mainly three methods for the synthesis of diaryl ketone compounds: Friedel–Crafts acylation reaction, halogenated arene carbonyl insertion coupling reaction and arene sp 2 Carbon–hydrogen bond direct acylation reaction. [0003] As the most traditional acylation method, Friedel–Crafts acylation reaction is carried out by Lewis acid (such as AlCl 3 , Fe...

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Problems solved by technology

[0003] As the most traditional acylation method, Friedel–Crafts acylation reaction is carried out by Lewis acid (such as AlCl 3 , FeCl 3 and TiCl 4 etc.) or strong protic acids (such as hydrofluoric acid, sulfuric acid, etc.) catalyze the electrophilic substitution reaction between the acylating reagent and the aromatic hydrocarbon; the post-treatment of the acid catalyst exists in the Friedel–Crafts acylation reaction, the substrate requires electro-richness, and the reaction Deficiencies such as high temperature and poor regioselectivity [Sartori, G., Maggi, R. Chem. Rev., 2006, 106, 1077]

Transition metal-catalyzed carbonyl intercalation coupling reaction has been established in recent years for the synthesis of highly selective and environmentally friendly carbonyl compounds; however, this method usually uses highly toxic CO as an important carbonyl source, which is incompatible with the current pursuit of green , The concept of environmental friendliness does not match [Wu, X.F., Neumann, H., Beller, M.Chem.Soc.Rev., 2011, 40, 4986]

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