Arene Diazonium Tetrafluoroborate Salts: Novel Lewis Acid Catalysts for Friedel-Crafts Alkylation of Indoles with alpha,beta-Unsaturated Ketones

摘要

In this study, the Friedel crafts alkylation of indole with alpha, beta-unsaturated ketones catalyzed by arene diazonium tetrafluoroborate salts is reported for the first time, and the optimal conditions of this reaction were explored. The experimental results show that the optimal conditions employed 10 mol % 2-(2-bromophenoxy)phenyl diazonium fluoborate (2) as a catalyst, CH3OH as a solvent, 60 degrees C as reaction temperature, and 24 h as reaction time. Under these optimized conditions, the reaction of indoles with various alpha,beta-unsaturated ketones can proceed smoothly to obtain aimed products (8). Yields of these reactions ranged from 60 % to 92 %. The reaction conditions are mild and the reaction operation is simple.