Journal
ORGANIC LETTERS
Volume 20, Issue 18, Pages 5648-5652Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02363
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Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIT) [2018R1A2B2004432]
- Korean Ministry of Education, Science, and Technology [2012M3A7B4049675]
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An efficient synthesis of highly pi-extended carbazoles is described via an unexpected domino [5 + 3 + 1] annulation approach. The Cu(I)-/base-promoted reactions of 2-nitrocinnamaldehydes with benzyl cyanides provide diverse benzo[b]carbazoles. The reaction is proposed to proceed via a sequential Michael addition/intramolecular addition of an enol into a nitro group, 6 pi- electrocyclization, and the final oxidative aromatization as supported by density functional theory calculations. Some of the synthesized carbazoles showed significant potential in fluorescence sensing of Cu2+ ions.
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