Cu-catalyzed decarboxylative iodination of aryl carboxylic acids with NaI: A practical entry to aryl iodides under aerobic conditions

被引：18

作者：

Fu, Zhengjiang ^{[1
]}

Jiang, Yongqing ^{[1
]}

Jiang, Ligao ^{[1
]}

Li, Zhaojie ^{[1
]}

Guo, Shengmei ^{[1
]}

Cai, Hu ^{[1
]}

机构：

[1] Nanchang Univ, Coll Chem, Nanchang 330031, Jiangxi, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 51期

基金：

中国国家自然科学基金;

关键词：

Cu catalyst; Decarboxylation; Iodination; Aryl iodide; Aerobic conditions; ONE-POT CONVERSION; COUPLING REACTIONS; ORGANIC POLLUTANTS; ELECTRON-RICH; STRATEGY; PHOTODEGRADATION; PHOTOREDUCTION; HALOGENATION;

D O I：

10.1016/j.tetlet.2018.11.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and practical Cu-catalyzed decarboxylative iodination has been well established under aerobic condition, which provides a useful method to synthesize aryl iodides in moderate to good yields with the use of (hetero)aryl carboxylic acids and NaI as starting materials. Thiabendazole has been prepared via a three-step procedure to show synthetic practicability of the protocol. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：4458 / 4461

页数：4

共 34 条

[1] A Novel Mode of Reactivity for Gold(I): The Decarboxylative Activation of (Hetero) Aromatic Carboxylic Acids [J].

Cornella, Josep ;

Rosillo-Lopez, Martin ;

Larrosa, Igor .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1359-1366

[2] Transition-Metal-Catalyzed Site-Selective C-H Halogenation Reactions [J].

Das, Riki ;

Kapur, Manmohan .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (08) :1524-1541

[3] Coupling of photodegradation of RhB with photoreduction of CO2 over rGO/SrTi0.95Fe0.05O3-δ catalyst: A strategy for one-pot conversion of organic pollutants to methanol and ethanol [J].

Dong, Wen-Hua ;

Wu, Dan -Dan ;

Luo, Jin-Min ;

Xing, Qiu-Ju ;

Liu, Hui ;

Zou, Jian-Ping ;

Luo, Xu-Biao ;

Min, Xiao-Bo ;

Liu, Hui -Long ;

Luo, Sheng-Lian ;

Au, Chak-Tong .

JOURNAL OF CATALYSIS, 2017, 349 :218-225

[4] Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions [J].

Fu, Zhengjiang ;

Jiang, Ligao ;

Zuo, Qianming ;

Li, Zhaojie ;

Liu, Yanzhu ;

Wei, Zhenhong ;

Cai, Hu .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (30) :5416-5421

[5] 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

[6] Recent Progress in Pd-Catalyzed Decarboxylative Coupling Reactions of (Hetero)aromatic Carboxylic Acids [J].

Fu, Zhengjiang ;

Li, Zhaojie ;

Xiong, Qiheng ;

Cai, Hu .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (05) :984-996

[7] Facile synthesis of 2,2′-dinitrosubstituted biaryls through Cu-catalyzed ligand-free decarboxylative homocoupling of ortho-nitrobenzoic acids [J].

Fu, Zhengjiang ;

Li, Zhaojie ;

Xiong, Qiheng ;

Cai, Hu .

RSC ADVANCES, 2015, 5 (64) :52101-52104

[8]

Hamamoto H., 2011, SYNLETT, V1563

[9] Gold-Catalysis: Reactions of Organogold Compounds with Electrophiles [J].

Hashmi, A. Stephen K. ;

Ramamurthi, Tanuja Dondeti ;

Todd, Matthew H. ;

Tsang, Althea S. -K. ;

Graf, Katharina .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2010, 63 (12) :1619-1626

[10] THE SANDMEYER REACTION [J].

HODGSON, HH .

CHEMICAL REVIEWS, 1947, 40 (02) :251-277

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