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

Title Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide.
Authors J. Li; W. Cong; Z. Gao; J. Zhang; H. Yang; G. Jiang
Journal Org Biomol Chem
DOI 10.1039/c8ob00318a
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.

Citation J. Li; W. Cong; Z. Gao; J. Zhang; H. Yang; G. Jiang.Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide.. Org Biomol Chem. 2018;16(18):34793486. doi:10.1039/c8ob00318a

Related Elements

Iodine

See more Iodine products. Iodine (atomic symbol: I, atomic number: 53) is a Block P, Group 17, Period 5 element with an atomic radius of 126.90447. The number of electrons in each of Iodine's shells is 2, 8, 18, 18, 7 and its electron configuration is [Kr] 4d10 5s2 5p5. The iodine atom has a radius of 140 pm and a Van der Waals radius of 198 pm. In its elemental form, iodine has a lustrous metallic gray appearance as a solid and a violet appearance as a gas or liquid solution. Elemental IodineIodine forms compounds with many elements, but is less active than the other halogens. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide. Iodine compounds are important in organic chemistry and very useful in the field of medicine. Iodine was discovered and first isolated by Bernard Courtois in 1811. The name Iodine is derived from the Greek word "iodes" meaning violet.

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