Catalytic Activities and Reaction Mechanism of the Synthesizing Bis(indolyl)methanes over Chalcocite
Bis(indolyl)methane is a very important compound,but its synthesis can release harmful substances and requires precious metals as catalysts.The combination of chalcocite/hydrogen peroxide could promote the re-action of N-methylindole and N,N-dimethylacetamide,achieving new and green synthesis of bis-substituted-in-dolylmethanes.After screening conditions including copper ore type,oxidant type and other factors,the suitable conditions were obtained:0.5 mmol N-methylindole,1.0 mL N,N-dimethylacetamide,20 mg chalcocite,1.0 mmol 30％hydrogen peroxide,reaction temperature 140 ℃,and reaction time 4 h.Under the optimal reaction conditions,it found that chalcocite can be run for 6 times without losing the activity,and N,N-dimethylacetamide can react with different substituted indoles to form 9 bis-substituted-indolylmethanes with yields ranging from 82％to 95％.Moreover,on the basis of control experiments and referring to relevant literatures,the reaction mecha-nism was proposed:N,N-dimethylacetamide underwent single electron transfers steps,following to electrophili-cally attack N-methylindole to form the product.Above all,this strategy provides theoretical basis and technical support for the green synthesis of bis-indole methane compounds.
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