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Issue 20, 2019
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Superbase-promoted selective carbon–carbon bond cleavage driven by aromatization

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Abstract

A novel selective carbon–carbon single bond cleavage has been disclosed through the copper-catalyzed reaction of 1-alkyl-3-alkylindolin-2-imine hydrochlorides with substituted 1-(bromomethyl)-2-iodobenzenes leading to fused N-heterocycles. Mechanistic studies showed that the intrinsic drive of aromatization and the action of the superbase derived from sodium tert-butoxide and dimethylsulfoxide were the key factors leading to the carbon–carbon single bond cleavage. Furthermore, the obtained N-heterocycles are indoloquinoline derivatives with wide biological activities.

Graphical abstract: Superbase-promoted selective carbon–carbon bond cleavage driven by aromatization

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Publication details

The article was received on 14 Mar 2019, accepted on 30 Apr 2019 and first published on 01 May 2019


Article type: Communication
DOI: 10.1039/C9OB00606K
Org. Biomol. Chem., 2019,17, 4984-4989

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    Superbase-promoted selective carbon–carbon bond cleavage driven by aromatization

    C. Liu, X. Zhu, Y. Han, H. Yang, C. Zhu and H. Fu, Org. Biomol. Chem., 2019, 17, 4984
    DOI: 10.1039/C9OB00606K

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