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Issue 18, 2018
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Rh(III)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide

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Abstract

A new approach for highly regioselective iodination of azobenzenes with alkyl iodide as the iodinating reagent enabled by Rh-catalyzed oxidative C–H activation has been developed. By changing the oxidant, various mono- and di-iodinated azobenzenes were smoothly obtained in moderate to excellent yields, respectively. The preliminary mechanistic study reveals that the reaction process might undergo electrophilic substitution of the directed ortho metalated five-membered rhodacycle compound by an iodine cationic species generated in situ from alkyl iodide and oxidant.

Graphical abstract: Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide

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Publication details

The article was received on 07 Feb 2018, accepted on 16 Apr 2018 and first published on 17 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00318A
Citation: Org. Biomol. Chem., 2018,16, 3479-3486
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    Rh(III)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide

    J. Li, W. Cong, Z. Gao, J. Zhang, H. Yang and G. Jiang, Org. Biomol. Chem., 2018, 16, 3479
    DOI: 10.1039/C8OB00318A

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