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Issue 79, 2018
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Rhodium(III)-catalyzed C–H activation at the C4-position of indole: switchable hydroarylation and oxidative Heck-type reactions of maleimides

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Abstract

A Rh(III)-catalyzed C–H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF3 group as a directing group. An additive plays an important role in switching the selectivity between 1,4-addition products and Heck-type products. An acid additive led to the formation of 1,4-addition products whereas a base additive promotes the formation of Heck-type products. Deuteration studies and control experiments were helpful to propose the mechanism.

Graphical abstract: Rhodium(iii)-catalyzed C–H activation at the C4-position of indole: switchable hydroarylation and oxidative Heck-type reactions of maleimides

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Publication details

The article was received on 01 Aug 2018, accepted on 06 Sep 2018 and first published on 06 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC06264A
Citation: Chem. Commun., 2018,54, 11200-11203
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    Rhodium(III)-catalyzed C–H activation at the C4-position of indole: switchable hydroarylation and oxidative Heck-type reactions of maleimides

    M. S. Sherikar, R. Kapanaiah, V. Lanke and K. R. Prabhu, Chem. Commun., 2018, 54, 11200
    DOI: 10.1039/C8CC06264A

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