Synthetic method and application of (1E, 2E)-1,2-bi(5-methoxyl-2-diphenylphosphine benzylidene) hydrazine

Abstract

(1E, 2E)-1,2-bi(5-methoxyl-2-diphenylphosphine benzylidene) hydrazine is a dual-phosphine ligand containing an imine group. An aromatic ring has methoxyl which supplies electrons so that double metal has the stronger coordination capability. According to the synthetic method, intermediate 5-methoxyl-2-(diphenylphosphino)benzaldehyde and hydrazine hydrate serve as raw materials, formic acid serves as a catalyst, and the raw materials and the formic acid flow back in methyl alcohol to obtain bis-imine bis-phosphine four-tooth ligand L. Bis-imine bis-phosphine four-tooth ligand L and Cu(CH3CN)4CIO4 in-situ catalytic Sonogashira cross coupling reaction is carried out, the catalytic system is very high (the yield reaches to 99%) in reactivity to aryl iodide and is active to aryl bromide to some degree, alkyne self-coupling products can be well avoided, the reactive system is simple, and post-processing is convenient. Adopted Cu is low in cost, easy to obtain, economical and clean, and takes part in the Sonogashira coupled reaction instead of expensive and toxicant Pd. No rganic amine used as a solvent or alkali is used. The (1E, 2E)-1,2-bi(5-methoxyl-2- diphenylphosphine benzylidene) hydrazine has very good application prospects in industrial production in the future.

Description

【Technical field】 [0001] The present invention relates to the preparation of catalyst ligands for cross-coupling reactions, especially a kind of imidophosphorus ligand (1E, 2E)-1,2-bis(5-methoxy-2-diphenylphosphino) The invention discloses a synthesis method and application of benzylidene hydrazine, belonging to the field of organic synthesis methodology. 【Background technique】 [0002] Due to their good coordination properties and rich coordination modes, organophosphine ligands have been widely used in medicine, pesticides and catalysis, and have always received more attention. Among them, nitrogen-phosphine ligands can be assembled with transition metal ions to obtain many metal complexes with novel structures and unique functions due to their multiple coordination sites, complex and variable coordination modes, and adjustable molecular deformability. The structure and catalytic properties of monodentate phosphine ligands and their metal complexes have been studied more ...

AI Technical Summary

Problems solved by technology

As the most commonly used metal catalyst in the Sonogashira reaction, Pd is not only expensive, highly toxic, and easy to remain in the product, but also prone to alkyne-alkyne self-coupling reactions

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