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Synthesis of Aryl Iodides from Arylhydrazines and Iodine.

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.

SUBMITTER: Dong CP

PROVIDER: S-EPMC6645010 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Synthesis of Aryl Iodides from Arylhydrazines and Iodine.

Dong Chun-Ping CP Nakamura Kentaro K Taniguchi Toshihide T Mita Soichiro S Kodama Shintaro S Kawaguchi Shin-Ichi SI Nomoto Akihiro A Ogawa Akiya A Mizuno Takumi T

ACS omega 20180823 8

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 I<sub>2</sub> 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 combi ...[more]

PMID: 31459110

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