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

页码：9312 / 9320

页数：9

共 88 条

[1] Aerobic Copper-Catalyzed Organic Reactions [J].

Allen, Scott E. ;

Walvoord, Ryan R. ;

Padilla-Salinas, Rosaura ;

Kozlowski, Marisa C. .

CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458

[2]

Axpana R., 2007, EUR J MED CHEM, V43, P1114

[3] Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly [J].

Bag, Sukdev ;

Patra, Tuhin ;

Modak, Atanu ;

Deb, Arghya ;

Maity, Soham ;

Dutta, Uttam ;

Dey, Aniruddha ;

Kancherla, Rajesh ;

Maji, Arun ;

Hazra, Avijit ;

Bera, Milan ;

Maiti, Debabrata .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) :11888-11891

[4] Synthesis of Difluoromethyl Thioethers from Difluoromethyl Trimethylsilane and Organothiocyanates Generated In Situ [J].

Bayarmagnai, Bilguun ;

Matheis, Christian ;

Jouvin, Kevin ;

Goossen, Lukas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5753-5756

[5]

Black L.A., 2009, [No title captured], Patent No. [WO 2009085945, 2009085945]

[6]

Boursalian GB, 2016, NAT CHEM, V8, P810, DOI [10.1038/nchem.2529, 10.1038/NCHEM.2529]

[7] Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives [J].

Castanheiro, Thomas ;

Suffert, Jean ;

Gulea, Mihaela ;

Donnard, Morgan .

ORGANIC LETTERS, 2016, 18 (11) :2588-2591

[8] Recent advances in the chemistry of organic thiocyanates [J].

Castanheiro, Thomas ;

Suffert, Jean ;

Donnard, Morgan ;

Gulea, Mihaela .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :494-505

[9] Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol [J].

Cheng, Chen ;

Hartwig, John F. .

SCIENCE, 2014, 343 (6173) :853-857

[10] Development of selective DprE1 inhibitors: Design, synthesis, crystal structure and antitubercular activity of benzothiazolylpyrimidine-5-carboxamides [J].

Chikhale, Rupesh ;

Menghani, Sunil ;

Babu, Ramavath ;

Bansode, Ratnadeep ;

Bhargavi, G. ;

Karodia, Nazira ;

Rajasekharan, M. V. ;

Paradkar, Anant ;

Khedekar, Pramod .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 96 :30-46

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