Abstract
3,3-Diaryloxidoles are prepared in high yields (62−99%) by reaction of isatin or substituted isatins with aromatics in triflic acid. The reaction shows a significant dependence on acid strength which suggests the formation of diprotonated, superelectrophilic intermediates. Reaction of isatin, benzene, and acid systems of varying strength (composed of CF3SO3H and CF3CO2H) showed that the acid strength must be more acidic than Ho = −11.5 for complete conversion to product. Reaction of isatins with mixtures of aromatics allows for the preparation of libraries of 3,3-diaryloxindole products by combinatorial synthesis.
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