Solvent-Free Indoles Addition to Carbonyl Compounds Promoted by CeCl₃·7H₂O-NaI-SiO₂: An Efficient Method for the Synthesis of Streptindole

 

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Abstract

Efficient electrophilic substitution reactions of indoles with various carbonyl compounds proceed easily in solvent-free conditions using CeCl₃·7H₂O-NaI-SiO₂ system promoter, to afford the corresponding bis(1H-indol-3-yl)alkanes in high yields. The synthetic value of the present procedure is demonstrated by the synthesis of streptindole (9), human intestinal bacteria metabolite.

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In our methodology of Lewis acid promoted solvent-free reaction the term ‘solvent-free’ refers solely to the reaction itself. On the other hand, preparation of initial adsorbate and purification of products invariably involve the use of solvent.