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Rh-Catalyzed C–H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration

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Abstract

Herein we demonstrate that an alkylation of indoles could be accessed through C–H bond functionalization with α,α-difluorovinyl tosylate. The key aspect for the effective alkylation is the influence of the fluorine substituents on the reactivity of the C[double bond, length as m-dash]C double bond, allowing regioselective insertion as well as an indolyl group shift process. Furthermore, the fluorides are removed through alcoholysis to furnish the alkylation product as a traceless auxiliary.

Graphical abstract: Rh-Catalyzed C–H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration

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Publication details

The article was received on 19 Mar 2018, accepted on 04 May 2018 and first published on 05 May 2018


Article type: Communication
DOI: 10.1039/C8CC02183J
Citation: Chem. Commun., 2018, Advance Article
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    Rh-Catalyzed C–H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration

    L. Zhou, C. Zhu, T. Loh and C. Feng, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC02183J

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