Catalytic reaction of aryldiazoacetates with indole and its derivatives: Profound effect of N-1 substitutent on the reaction pathways

Abstract

The reaction of indole and its derivatives with aryldiazoacetates has been studied in the presence of copper and rhodium catalysts. The electronic property of N-1 substitutent showed significant effect on the reaction pathways. The electron-donating group favored the formation of the β-alkylation products, while the electron-withdrawing group favored the formation of the cyclopropane products. A reaction mechanism was proposed based on the experimental data and previous research results. The structure of aryl group in diazo compounds also affected the yield of the β-alkylation products or the cyclopropane products. © 2008 SIOC, CAS, & Wiley-VCH Verlag GmbH & Co. KGaA.