Electrochemical synthesis of benzoxazoles mediated by 2,3-dichloro-5,6-dicyano-p-hydroquinone (DDH) as a redox catalyst

被引：16

作者：

Kang, Li-Shuo ^{[1
]}

Xiao, Huan-lan ^{[1
]}

Zeng, Cheng-Chu ^{[1
]}

Hu, Li-Ming ^{[1
]}

Little, R. Daniel ^{[2
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

[2] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF ELECTROANALYTICAL CHEMISTRY | 2016年 / 767卷

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

Indirect electrolysis; 2,3-Dichloro-5,6-dicyano-p-hydroquinone (DDH); 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ); Benzoxazole; Schiff base; C-H BONDS; 2-SUBSTITUTED BENZOXAZOLES; FACILE PREPARATION; POWERFUL CATALYST; OXIDATION; TRIARYLIMIDAZOLE; BENZOTHIAZOLES; ARYLATION; POTENT; BENZIMIDAZOLES;

D O I：

10.1016/j.jelechem.2015.12.051

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

A novel electrochemical strategy for the efficient synthesis of benzoxazoles has been developed. The chemistry is performed in a beaker-type undivided cell under constant current electrolysis conditions, utilizing 2,3-dichloro-5,6-dicyano-p-hydroquinone (DDH) as a redox catalyst. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：13 / 17

页数：5

共 48 条

[11] Metal-Free Oxidative Cyclization of Urea-Tethered Alkenes with Hypervalent Iodine [J].

Cochran, Brian M. ;

Michael, Forrest E. .

ORGANIC LETTERS, 2008, 10 (21) :5039-5042

[12] Selective Oxidation of Benzylic and Allylic Alcohols Using Mn(OAc)3/Catalytic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone [J].

Cosner, Casey C. ;

Cabrera, Pablo J. ;

Byrd, Katherine M. ;

Thomas, Asia M. Adams ;

Helquist, Paul .

ORGANIC LETTERS, 2011, 13 (08) :2071-2073

[13] Biomimetic Oxidative Coupling of Benzylamines and 2-Aminophenols: Synthesis of Benzoxazoles [J].

Endo, Yoshinori ;

Backvall, Jan-E. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (43) :13609-13613

[14] Highly Stereoselective Metal-Free Oxyaminations Using Chiral Hypervalent Iodine Reagents [J].

Farid, Umar ;

Wirth, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) :3462-3465

[15] Redox catalysis in organic electrosynthesis: basic principles and recent developments [J].

Francke, Robert ;

Little, R. Daniel .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2492-2521

[16] Electrochemically Initiated Oxidative Amination of Benzoxazoles Using Tetraalkylammonium Halides As Redox Catalysts [J].

Gao, Wei-Jing ;

Li, Wei-Cui ;

Zeng, Cheng-Chu ;

Tian, Hong-Yu ;

Hu, Li-Ming ;

Little, R. Daniel .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) :9613-9618

[17] Oxidative and Enantioselective Cross-Coupling of Aldehydes and Nitromethane Catalyzed by Diphenylprolinol Silyl Ether [J].

Hayashi, Yujiro ;

Itoh, Takahiko ;

Ishikawa, Hayato .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) :3920-3924

[18] CuO nano-particles supported on silica, a new catalyst for facile synthesis of benzimidazoles, benzothiazoles and benzoxazoles [J].

Inamdar, Suleman M. ;

More, Vinod K. ;

Mandal, Sisir K. .

TETRAHEDRON LETTERS, 2013, 54 (06) :579-583

[19]

Julia R.K., 2014, J AM CHEM SOC, V136, P2998

[20] Chlorination and ortho-acetoxylation of 2-arylbenzoxazoles [J].

Leng, Yuting ;

Yang, Fan ;

Zhu, Weiguo ;

Wu, Yangjie ;

Li, Xiang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5288-5296

← 1 2 3 4 5 →