Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics

被引：106

作者：

Jiang, Huanfeng ^{[1
]}

Yu, Wentao ^{[1
]}

Tang, Xiaodong ^{[1
]}

Li, Jianxiao ^{[1
]}

Wu, Wanqing ^{[1
]}

机构：

[1] South China Univ Technol, Key Lab Funct Mol Engn Guangdong Prov, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 18期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; BOND FUNCTIONALIZATION; DIFLUOROMETHYL THIOETHERS; AMMONIUM THIOCYANATE; EFFICIENT SYNTHESIS; VERSATILE REAGENT; FACILE SYNTHESIS; MILD CONDITIONS; ARENES; CHEMISTRY;

D O I：

10.1021/acs.joc.7b01122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O-2 as the oxidant. The combination of Cu(OTf)(2), N,N,N',N'-tetramethylethylenediamine (TMEDA) and BF3 center dot Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.

引用

收藏

页码：9312 / 9320

页数：9

相关论文

共 88 条

[81] Mild Copper-Mediated Fluorination of Aryl Stannanes and Aryl Trifluoroborates [J].

Ye, Yingda ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4648-4651

[82] Highly Site-Selective Direct C-H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis [J].

Yu, Zhunzhun ;

Ma, Ben ;

Chen, Mingjin ;

Wu, Hai-Hong ;

Liu, Lu ;

Zhang, Junliang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (19) :6904-6907

[83] An efficient and regioselective thiocyanation of aromatic and heteroaromatic compounds using cross-linked poly (4-vinylpyridine)-supported thiocyanate as a versatile reagent and potassium peroxydisulfate as a strong oxidizing agent [J].

Zarchi, M. A. Karimi ;

Banihashemi, R. .

JOURNAL OF SULFUR CHEMISTRY, 2014, 35 (04) :458-469

[84] Thiocyanation of aromatic and heteroaromatic compounds using polymer-supported thiocyanate ion as the versatile reagent and ceric ammonium nitrate as the versatile single-electron oxidant [J].

Zarchi, Mohammad Ali Karimi ;

Banihashemi, Reza .

JOURNAL OF SULFUR CHEMISTRY, 2016, 37 (03) :282-295

[85] Recent advances in copper-catalyzed dehydrogenative functionalization via a single electron transfer (SET) process [J].

Zhang, Chun ;

Tang, Conghui ;

Jiao, Ning .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3464-3484

[86] Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines Leading to Aromatic Azo Compounds using Dioxygen as an Oxidant [J].

Zhang, Chun ;

Jiao, Ning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) :6174-6177

[87] Copper/N, N, N′, N′-Tetramethylethylenediamine-Catalyzed Synthesis of N-Substituted Benzoheterocycles via C-S Cross-Coupling at Ambient Temperature in Water [J].

Zhao, Na ;

Liu, Liang ;

Wang, Fei ;

Li, Jia ;

Zhang, Wu .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) :2575-2579

[88] para-Selective C-H bond functionalization of iodobenzenes [J].

Zhao, Ying ;

Yan, Haiming ;

Lu, Hanwei ;

Huang, Zhiliang ;

Lei, Aiwen .

CHEMICAL COMMUNICATIONS, 2016, 52 (76) :11366-11369

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