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Issue 9, 2013
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One-shot indole-to-carbazole π-extension by a Pd–Cu–Ag trimetallic system

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Abstract

We have developed a Pd–Cu–Ag trimetallic system that can convert indoles to carbazoles using electron-deficient alkenes as two-carbon units. Investigation of the reaction mechanism revealed that this one-shot indole-to-carbazole π-extension is likely to proceed through the sequence of (i) Pd/Cu-catalyzed indole C–H alkenylation, (ii) Ag-promoted Diels–Alder reaction and dehydrogenative aromatization. The successful one-pot synthesis of a granulatimide derivative, an interesting class of Chk1 kinase inhibitor, highlights the potential of the present reaction for further development and applications.

Graphical abstract: One-shot indole-to-carbazole π-extension by a Pd–Cu–Ag trimetallic system

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Publication details

The article was received on 23 May 2013, accepted on 18 Jun 2013 and first published on 19 Jun 2013


Article type: Edge Article
DOI: 10.1039/C3SC51447A
Citation: Chem. Sci., 2013,4, 3416-3420
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    One-shot indole-to-carbazole π-extension by a Pd–Cu–Ag trimetallic system

    K. Ozaki, H. Zhang, H. Ito, A. Lei and K. Itami, Chem. Sci., 2013, 4, 3416
    DOI: 10.1039/C3SC51447A

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