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Issue 45, 2018
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Rh(III)-Catalyzed dual C–H functionalization of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds toward polysubstituted carbazoles

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Abstract

A rhodium-catalyzed annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds has been developed, leading to a series of polysubstituted carbazoles in moderate to good yields. This procedure proceeded with formal Rh(III)-catalyzed (4 + 2) cycloaddition, with the functionalization of 2-C–H bonds of indole in a step-economical procedure. Additionally, this reaction could also be conducted under acidic conditions when diazo compounds were employed as the reaction partners, which was a complement to the annulation of sulfoxonium ylides under weak basic conditions.

Graphical abstract: Rh(iii)-Catalyzed dual C–H functionalization of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds toward polysubstituted carbazoles

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Publication details

The article was received on 31 Aug 2018, accepted on 01 Nov 2018 and first published on 05 Nov 2018


Article type: Communication
DOI: 10.1039/C8OB02145G
Org. Biomol. Chem., 2018,16, 8715-8718

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    Rh(III)-Catalyzed dual C–H functionalization of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds toward polysubstituted carbazoles

    Y. Xiao, H. Xiong, S. Sun, J. Yu and J. Cheng, Org. Biomol. Chem., 2018, 16, 8715
    DOI: 10.1039/C8OB02145G

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