Synthesis of Aryl Iodides from Arylhydrazines and Iodine

Chun-Ping Dong; Kentaro Nakamura; Toshihide Taniguchi; Soichiro Mita; Shintaro Kodama; Shin-Ichi Kawaguchi; Akihiro Nomoto; Akiya Ogawa; Takumi Mizuno

doi:10.1021/acsomega.8b01559

Synthesis of Aryl Iodides from Arylhydrazines and Iodine

ACS Omega. 2018 Aug 23;3(8):9814-9821. doi: 10.1021/acsomega.8b01559. eCollection 2018 Aug 31.

Authors

Chun-Ping Dong¹, Kentaro Nakamura¹, Toshihide Taniguchi², Soichiro Mita¹, Shintaro Kodama¹, Shin-Ichi Kawaguchi³, Akihiro Nomoto¹, Akiya Ogawa¹, Takumi Mizuno⁴

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
² Seika Corporation, 1-1-82 Kozaika, Wakayama 641-0007, Japan.
³ Center for Education and Research in Agricultural Innovation, Faculty of Agriculture, Saga University, 152-1 Shonan-cho, Karatsu, Saga 847-0021, Japan.
⁴ Morinomiya Center, Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan.

Abstract

A metal- and base-free method is developed for the synthesis of aryl iodides from arylhydrazine hydrochlorides and iodine. A wide variety of aryl iodides can be conveniently synthesized by an equimolar reaction of arylhydrazine hydrochlorides and I₂ in dimethyl sulfoxide at 60 °C for 6 h. In the iodination step, arylhydrazines are oxidized by iodine to form arenediazonium salts, which undergo single-electron transfer from iodide anion to give aryl and iodine radicals; subsequent combination of them affords the corresponding aryl iodides.