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Issue 20, 2018
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Copper-mediated domino C–H iodination and nitration of indoles

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Abstract

An efficient and cost-effective copper-mediated aerobic oxidative C–H iodination and nitration of indoles via double C–H functionalization is reported. The domino process proceeds smoothly under mild aerobic conditions to give 3-iodo-2-nitroindoles in one step with high regioselectivity and a broad substrate scope. The mechanism of the iodination step is proposed to proceed via a Cu(III)-iodide species that undergoes electrophilic addition at the C3 position of the indole motif. The subsequent nitration step involves a sequence of C–H activation, nitro radical oxidative addition, and reductive elimination.

Graphical abstract: Copper-mediated domino C–H iodination and nitration of indoles

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Supplementary files

Article information


Submitted
12 Jan 2018
Accepted
12 Feb 2018
First published
12 Feb 2018

Chem. Commun., 2018,54, 2514-2517
Article type
Communication

Copper-mediated domino C–H iodination and nitration of indoles

D. Tu, J. Luo and C. Jiang, Chem. Commun., 2018, 54, 2514
DOI: 10.1039/C8CC00267C

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