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

A technology of diphenylphosphinobenzylidene and diphenylphosphino, which is applied in the field of preparation of imidophosphorus ligand-1 and catalyst ligand, and can solve the problem of high price, product residue, alkyne-alkyne self-coupling The problem of joint reaction and other problems is achieved, the reaction system is simple, the post-treatment is convenient, and the effect of avoiding alkyne self-coupling products

Inactive Publication Date: 2014-01-01
NANKAI UNIV
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  • Abstract
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Problems solved by technology

As the most commonly used metal catalyst in the Sonogashira reaction, Pd is not only expensive, high

Method used

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

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Embodiment

[0033] A kind of synthetic method of described (1E, 2E)-1,2-bis(5-methoxy-2-diphenylphosphinobenzylidene)hydrazine is as follows:

[0034] (1) Preparation of 5-methoxy-2-diphenylphosphinobenzaldehyde

[0035] 1) At room temperature, in a 500ml three-neck round bottom flask, add m-methoxybenzaldehyde (60.6g, 446mmol), glacial acetic acid (100ml), after stirring evenly, slowly drop liquid bromine (27.5ml, 536mmol) into the solution ), dropwise, stirred at room temperature for 36 hours. After the reaction, the reaction liquid was quenched with 500 ml of saturated sodium sulfite solution, then poured into 200 ml of water, extracted with ether, the combined organic phase was washed with water and saturated brine, separated, and the organic phase was dried with anhydrous magnesium sulfate. Filtration and removal of the solvent gave 81.48 g (85%) of a dark yellow solid. The melting point is 71-76°C. 1 HNMR (400MHz, CDCl 3 )δ10.32(s, 1H, CHO), 7.53(d, J=8.8Hz, 1H, Ph-H), 7.42(d, J...

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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 ...

Claims

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Application Information

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IPC IPC(8): C07F9/50C07F19/00B01J31/22C07C15/54C07C2/86C07C17/266C07C25/02C07C205/06C07C201/12C07C205/35C07C205/12C07C211/52C07C217/80C07C213/08
Inventor 徐凤波张春来朱佳芳王文虎李庆山胡方中祝冠彬
Owner NANKAI UNIV
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