Methods of preparing organic boron compound and beta-carbonyl compound by catalyzing copper ion loaded chitosan microspheres

Abstract

The invention relates to methods of preparing an organic boron compound and a beta-carbonyl compound by catalyzing copper ion loaded chitosan microspheres. The preparation method of the organic boroncompound mainly comprises the following steps of A, adding copper ion loaded chitosan microspheres, tetrahydrofuran and water into a reaction vessel, and fully stirring to obtain a mixed solution under room temperature; B, adding an alpha,beta-unsaturated carbonyl compound and a bis(pinacolato)diboron reagent into the mixed solution; C, stirring at room temperature so as to react fully; and D, after the reaction is finished, separating and purifying to obtain the organic boron compound. The preparation method of the beta-carbonyl compound comprises the steps A, B and C of the above method, andalso comprises steps of directly filtering, then washing with tetrahydrofuran and mixing a washing liquid with a filtrate, adding sodium perborate tetrahydrate into the filtrate, stirring at room temperature so as to react fully, separating and purifying to obtain the beta-carbonyl compound. The methods have the beneficial effects that the copper ion loaded chitosan microspheres are used as a catalyst to prepare the organic boron compound for the first time, no extra ligand is added, and the methods have high catalysis efficiency, high stability, and is non-toxic and environmentally friendly.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for catalytically preparing organic boron compounds and beta-hydroxyl compounds by chitosan microspheres loaded with copper ions. Background technique [0002] Organoboron compounds are an important class of intermediates that widely exist in the structures of natural products and drug molecules. They are also important synthons in organic synthesis. C-B bonds can be further converted into C-O, C-N bonds and C-C bonds. Compared with the traditional method of using equivalent reagents, the strategy of direct boron addition to unsaturated carbonyl compounds under the action of catalysts is more direct and effective, and has attracted extensive attention in recent years. Most of the catalysts used in the literature are expensive transition metals, such as Rh, Ni, Pt, Pb, etc., which are expensive and not suitable for actual production. In addition, there is als...

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Problems solved by technology

[0005] The invention provides a method for preparing organoboron compounds and β-hydroxyl compounds by loading copper ion-loaded chitosan microspheres, aiming at at least to a certain extent overcoming the following deficiencies in the prior art: using precious metals as catalysts for synthesizing organoboron compounds Or when the equivalent reagent is a synthetic raw material, the cost is high and cannot be industrialized; when using monovalent copper and nitrogen carbene ligands as a catalyst, the operation process is complicated, requiring a strong base (potassium tert-butoxide, etc.), low temperature (-78 ° C), Harsh conditions such as strict anhydrous also lead to high production costs; if the existing β-hydroxy compound is prepared from the organoboron compound, it means that the organoboron compound needs to be separated and purified from the reaction product after synthesis , there is no continuous production, so the process route is complicated and the production efficiency is low

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