An efficient metal-free strategy for the synthesis of pharmaceutically relevant benzo[α]carbazoles from the derivatives of readily available 2-phenylindole and bio-renewable acetol in an aqueous biphasic system was d...An efficient metal-free strategy for the synthesis of pharmaceutically relevant benzo[α]carbazoles from the derivatives of readily available 2-phenylindole and bio-renewable acetol in an aqueous biphasic system was developed. This protocol employed a sulfone-containing Bronsted acidic ionic liquid as the catalyst, which could be used for five times without a noticeable decrease in its activity and selectivity. Various substituted 2-phenylindoles and α-hydroxyketones participated in the reaction smoothly, with water as the sole byproduct. Mechanistically, the reaction involved the conventional carbon-nucleophile-induced Heyns-type rearrangement and downstream intramolecular olefination.展开更多
基金supported by the National Natural Science Foundation of China(21761132014,21872060)the Fundamental Research Funds for the Central Universities of China(2016YXZD033)+1 种基金the Fundamental Research Funds for the Central Universities(2019kfyXJJS072)Opening fund of Hubei Key Laboratory of Material Chemistry and Service Failure(2017MCF01K)~~
文摘An efficient metal-free strategy for the synthesis of pharmaceutically relevant benzo[α]carbazoles from the derivatives of readily available 2-phenylindole and bio-renewable acetol in an aqueous biphasic system was developed. This protocol employed a sulfone-containing Bronsted acidic ionic liquid as the catalyst, which could be used for five times without a noticeable decrease in its activity and selectivity. Various substituted 2-phenylindoles and α-hydroxyketones participated in the reaction smoothly, with water as the sole byproduct. Mechanistically, the reaction involved the conventional carbon-nucleophile-induced Heyns-type rearrangement and downstream intramolecular olefination.
