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Copper-Catalyzed Three-Component Formal [3 + 1 + 2] Benzannulation for Carbazole and Indole Synthesis
Tenglong Guo1, Li Han2, Tingpeng Wang1
1Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, People's Republic of China.
Abstract:
Three-component formal [3 + 1 + 2] benzannulation reactions of indole-3-carbaldehydes or 1-methyl-pyrrole-2-carbaldehydes with two different molecules of saturated ketones have been successfully developed under Cu-catalyzed and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated conditions. Various unsymmetrically substituted carbazoles and indoles were obtained up to 95% yield. Furthermore, the resulting products exhibit unusual aggregation-induced emission (AIE) properties in the solid state. This method features high atom-economy, cheap catalysts and oxidants, wide substrate scope, and saturated ketones as one-carbon and two-carbon sources, thus providing an efficient approach to polycyclic carbazole and indole compounds.
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