Synthesis of Aryl Iodides from Arylhydrazines and Iodine

被引：26

作者：

Dong, Chun-ping ^{[1
]}

Nakamura, Kentaro ^{[1
]}

Taniguchi, Toshihide ^{[2
]}

Mita, Soichiro ^{[1
]}

Kodama, Shintaro ^{[1
]}

Kawaguchi, Shin-ichi ^{[3
]}

Nomoto, Akihiro ^{[1
]}

Ogawa, Akiya ^{[1
]}

Mizuno, Takumi ^{[4
]}

机构：

[1] Osaka Prefecture Univ, Dept Appl Chem, Grad Sch Engn, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan

[2] Seika Corp, 1-1-82 Kozaika, Wakayama 6410007, Japan

[3] Saga Univ, Fac Agr, Ctr Educ & Res Agr Innovat, 152-1 Shonan Cho, Karatsu, Shiga 8470021, Japan

[4] Osaka Res Inst Ind Sci & Technol, Morinomiya Ctr, Joto Ku, 1-6-50 Morinomiya, Osaka 5368553, Japan

来源：

ACS OMEGA | 2018年 / 3卷 / 08期

基金：

日本学术振兴会;

关键词：

AROMATIC FINKELSTEIN REACTION; TRANSITION-METAL-FREE; ONE-POT SYNTHESIS; C-H ARYLATION; ARYLBORONIC ACIDS; CROSS-COUPLINGS; IONIC LIQUID; IODINATION; EFFICIENT; HALOGENATION;

D O I：

10.1021/acsomega.8b01559

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-2 in dimethyl sulfoxide at 60 degrees 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.

引用

页码：9814 / 9821

页数：8

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