Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide. Issue 18 (24th April 2018)

• Record Type: Journal Article
• Authors: Li, Jixing; Cong, Wenxia; Gao, Zeng; Zhang, Jinlong; Yang, Huameng; Jiang, Gaoxi
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 18(2018)
• Page Start: 3479
• Page End: 3486
• Publication Date: 2018-04-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00318a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We developed a highly chemoselective oxidative access to ortho -iodinated azobenzenes by Rh(iii )-catalysis with alkyl iodide as the iodinating reagent. 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.