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Issue 47, 2017
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Rhodium-catalyzed C2 and C4 C–H activation/annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes: a facile access to substituted and fused carbazoles

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Abstract

Rhodium-catalyzed oxidative annulation reactions of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes have been developed. A series of substituted carbazoles and 4H-oxepino[2,3,4,5-def]carbazoles, through a formal Rh(III)-catalyzed (4+2) cycloaddition with an alkyne and tandem (4+2) and (5+2) cycloaddition with two molecules of alkynes, were obtained. The reactions involved sequential cleavage of C(sp2)–H/C(sp3)–H bonds and annulation with an alkyne in the first step, and sequential cleavage of C(sp2)–H/O–H bonds and annulation with another alkyne in the second step. Some of the 4H-oxepino[2,3,4,5-def]carbazole products exhibit intense fluorescence in the solid state.

Graphical abstract: Rhodium-catalyzed C2 and C4 C–H activation/annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes: a facile access to substituted and fused carbazoles

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Publication details

The article was received on 13 Apr 2017, accepted on 18 May 2017 and first published on 18 May 2017


Article type: Communication
DOI: 10.1039/C7CC02808C
Citation: Chem. Commun., 2017,53, 6343-6346
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    Rhodium-catalyzed C2 and C4 C–H activation/annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes: a facile access to substituted and fused carbazoles

    T. Zhou, B. Li and B. Wang, Chem. Commun., 2017, 53, 6343
    DOI: 10.1039/C7CC02808C

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