Issue 20, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
12 Jan 2018
Accepted
12 Feb 2018
First published
12 Feb 2018

Chem. Commun., 2018,54, 2514-2517

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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