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Note | Regular issue | Vol 81, No. 4, 2010, pp.977-984
Published online, 19th February, 2010
DOI: 10.3987/COM-09-11892
A Novel Approach to Diindenocarbazoles via Palladium-Catalyzed Intramolecular Arylation

Lingling Rong, Qiancai Liu,* Jie Tang, and Zhenguo Chi

*Department of Chemistry, East China Normal University, 3663 Zhongshan RD(N9, Shanghai 200062, China


The diindenocarbazole derivatives are synthesized by the reaction of 2,7-dibromo-9-hexylcarbazole with benzoyl chloride under Friedel-Crafts conditions, followed by Wolff-Kishner-Huang reduction to produce 3,6-dibenzyl-2,7-dibromo-9-hexylcarbazole, which was cyclized to form bis(indeno)-9-hexylcarbazole by palladium-catalyzed double intramolecular arylation. The diindeno-carbazole was further converted into fully alkylated compounds.