Palladium Acetate catalyzed C-2 and C-3 allylation of indoles

Document Type : Research and Reference

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1 chemistry department, faculty of science, tanta university, tanta, egypt

2 Chemistry department, Tanta University, faculty of science, tanta, egypt

Abstract

The allylation of indole and indole derivatives with allyl alcohol, where C3 and C2 selectivity was recognized for NH indole and indole derivatives, was achieved by Palladium acetate as a catalyst. The reaction was controlled at 40 °C in the presence of PBr3 and NaOH as a base. Pd-acetate catalyzed the allylation of indoles and indole derivatives with allylic alcohols and the reaction occurs by the dimerization at the C3 and C2 positions of the indole, this efficient way has been developed by homo coupling of indoles to give 3-(1-(indolin-2-yl)allyl)-1H-indole as a product that can be used as an intermediate for the preparation of several kinds of pharmaceutical compounds. The chemical structure of the product was elucidated using 1H-NMR, 13C-NMR, and MS spectroscopies. The study of Molecular docking provided that 3-(1-(indolin-2-yl)allyl)-1H-indole possess potent binding to the aspartic protease with binding energy -5.6 kcal/mol, which qualifies it as a promising anti-fungal agent.

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