Metal free access to amide compounds via peroxide-mediated N=N double bond cleavage of azobenzenes

被引：17

作者：

Hong, Gang ^{[1
]}

Mao, Dan

Zhu, Xiaoyan

Wu, Shengying

Wang, Limin

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 08期

关键词：

CATALYZED OXIDATIVE AMIDATION; AZO-COMPOUNDS; REDUCTIVE CLEAVAGE; ORTHO-ACYLATION; ALDEHYDES; AMINES; ACETANILIDES; DERIVATIVES; INDAZOLES; ZINC;

D O I：

10.1039/c5qo00125k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct amidation of aldehydes or benzylamines with azobenzenes through TBHP-mediated N=N double bond cleavage of azobenzenes has been developed. A series of amide compounds with a wide range of functionalities were obtained with moderate to good yields. To the best of our knowledge, this is the first example of the N=N double bond cleavage of azobenzenes used in synthesizing amide compounds.

引用

页码：985 / 989

页数：5

共 44 条

[1] Metal-catalysed approaches to amide bond formation [J].

Allen, C. Liana ;

Williams, Jonathan M. J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415

[2] Synthesis and optical properties of NLO chromophores containing an indoline donor and azo linker [J].

Ashraf, Mohamed ;

Teshome, Ayele ;

Kay, Andrew J. ;

Gainsford, Graeme J. ;

Bhuiyan, M. Delower H. ;

Asselberghs, Inge ;

Clays, Koen .

DYES AND PIGMENTS, 2012, 95 (03) :455-464

[3]

Bafana A, 2011, ENVIRON REV, V19, P350, DOI [10.1139/A11-018, 10.1139/a11-018]

[4] Photochromic Blockers of Voltage-Gated Potassium Channels [J].

Banghart, Matthew R. ;

Mourot, Alexandre ;

Fortin, Doris L. ;

Yao, Jennifer Z. ;

Kramer, Richard H. ;

Trauner, Dirk .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9097-9101

[5] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes [J].

Basle, Olivier ;

Bidange, Johan ;

Shuai, Qi ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) :1145-1149

[6] Reducing degradation of azo dye by zero-valent iron in aqueous solution [J].

Cao, JS ;

Wei, LP ;

Huang, QG ;

Wang, LS ;

Han, SK .

CHEMOSPHERE, 1999, 38 (03) :565-571

[7]

Cupido T, 2007, CURR OPIN DRUG DISC, V10, P768

[8] Stereoselective synthesis of α- and β-glycosylamide derivatives from glycopyranosyl azides via isoxazoline intermediates [J].

Damkaci, F ;

DeShong, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) :4408-4409

[9] Copper-catalyzed oxidative amidation between aldehydes and arylamines under mild conditions [J].

Ding, Yongzheng ;

Zhang, Xian ;

Zhang, Dongyang ;

Chen, Yuting ;

Wu, Zhibing ;

Wang, Peiyi ;

Xue, Wei ;

Song, Baoan ;

Yang, Song .

TETRAHEDRON LETTERS, 2015, 56 (06) :831-833

[10] Metal-catalyzed amide bond forming reactions in an environmentally friendly aqueous medium: nitrile hydrations and beyond [J].

Garcia-Alvarez, Rocio ;

Crochet, Pascale ;

Cadierno, Victorio .

GREEN CHEMISTRY, 2013, 15 (01) :46-66

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