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.