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

共 54 条

[1] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].

Antilla, JC ;

Baskin, JM ;

Barder, TE ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587

[2] N-Iodosuccinimide (NIS) in Direct Aromatic Iodination [J].

Bergstrom, Maria ;

Suresh, Ganji ;

Naidu, Veluru Ramesh ;

Unelius, C. Rikard .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (22) :3234-3239

[3] Polyethylene Glycol Nitrite (PEG-ONO) as a Novel Diazotizing Agent [J].

Bochare, Machhindra D. ;

Degani, Mariam S. .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (05) :3716-3720

[4] Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides [J].

Cant, Alastair A. ;

Bhalla, Rajiv ;

Pimlott, Sally L. ;

Sutherland, Andrew .

CHEMICAL COMMUNICATIONS, 2012, 48 (33) :3993-3995

[5] Nitrite ionic liquid as a new reagent for in situ synthesis of aryl iodides and azides [J].

Eshghi, Hossein ;

Bakavoli, Mehdi ;

Ghasemzadeh, Marjan .

RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (06) :3999-4007

[6]

Friedrich W., 1956, CHEM BER, V89, P1994

[7] Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions [J].

Fu, Zhengjiang ;

Li, Zhaojie ;

Song, Yuanyuan ;

Yang, Ruchun ;

Liu, Yanzhu ;

Cai, Hu .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (07) :2794-2803

[8] 4-Substituted tert-Butyl Phenylazocarboxylates-Synthetic Equivalents for the para-Phenyl Radical Cation [J].

Hoefling, Sarah B. ;

Bartuschat, Amelie L. ;

Heinrich, Markus R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) :9769-9772

[9] Unexpected, drastic effect of triflic acid on oxidative diacetoxylation of iodoarenes by sodium perborate. A facile and efficient one-pot synthesis of (diacetoxyiodo)arenes [J].

Hossain, D ;

Kitamura, T .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6984-6986

[10] Highly active recyclable heterogeneous Pd/ZnO nanoparticle catalyst: sustainable developments for the C-O and C-N bond cross-coupling reactions of aryl halides under ligand-free conditions [J].

Hosseini-Sarvari, Mona ;

Razmi, Zahra .

RSC ADVANCES, 2014, 4 (83) :44105-44116

← 1 2 3 4 5 6 →