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

Jixing Li; Wenxia Cong; Zeng Gao; Jinlong Zhang; Huameng Yang; Gaoxi Jiang

doi:10.1039/C8OB00318A

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

Jixing Li,*^a Wenxia Cong,^a Zeng Gao,^b^c Jinlong Zhang,^b Huameng Yang^b and Gaoxi Jiang*^b

Author affiliations

* Corresponding authors

^a School of Chemistry & Chemical Engineering, Linyi University, Linyi 276005, P. R. China
E-mail: jxli1987123@126.com

^b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. China
E-mail: gxjiang@licp.cas.cn

^c University of Chinese Academy of Sciences, Beijing 100049, P. R. China

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.

This article is part of the themed collection: Synthetic methodology in OBC

Supplementary files

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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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Publication details

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

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