3 years ago

Modular Synthesis of Carbazole-Based Conjugated Molecules through a One-Pot Annulation/Dehydrogenation Sequence

Modular Synthesis of Carbazole-Based Conjugated Molecules through a One-Pot Annulation/Dehydrogenation Sequence
Shanping Chen, Liren Wang, Zhaoran Hao, Huawen Huang, Jing Zhang, Guo-Jun Deng
An efficient one-pot indole-to-carbazole strategy with cyclohexanones as the aryl source is described. This cascade carbazole formation is enabled by the NH4I-catalyzed annulation of indoles, cyclohexanones, and alkenes and subsequent dehydrogenative aromatization. The present work provides a modular synthesis of arylcarbazoles, benzocarbazoles, and naphthocarbazoles with excellent regioselectivity and broad functional group tolerance. More than 40 benzo-fused carbazoles were synthesized, and the UV–vis absorption and photoluminescent spectra of some products were measured to study their photophysical properties.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02305

DOI: 10.1021/acs.joc.7b02305

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