Iron-catalyzed C-N bond formation via oxidative Csp3-H bond functionalization adjacent to nitrogen in amides and anilines: Synthesis of N-alkyl and N-benzyl azoles

被引：24

作者：

Saidulu, G. ^{[1
]}

Kumar, R. Arun ^{[1
]}

Reddy, K. Rajender ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Inorgan & Phys Chem Div, Hyderabad 500007, Telangana State, India

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 28期

关键词：

Iron; Oxidative coupling; Peroxide; Carbon-nitrogen bond; Azole; DEHYDROGENATIVE COUPLING REACTION; H BOND; TERTIARY-AMINES; VISIBLE-LIGHT; HETEROCYCLIC CARBENES; ANTIFUNGAL AGENTS; MOLECULAR DOCKING; HYDROGEN-PEROXIDE; ACTIVATION; DERIVATIVES;

D O I：

10.1016/j.tetlet.2015.05.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iron catalyzed oxidative protocol was developed to couple azoles with amides to generate N-alkylazole derivatives in moderate to excellent yields using tertiarybutyl hydroperoxide as an oxidant under mild reaction conditions. Furthermore, this protocol explored to couple azoles with N-alkylanilines, unexpectedly N-benzyl azoles were obtained as major products under these oxidative conditions. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4200 / 4203

页数：4

共 73 条

[51] Iron-Catalyzed Oxidative Coupling of Alkylamides with Arenes through Oxidation of Alkylamides Followed by Friedel-Crafts Alkylation [J].

Shirakawa, Eiji ;

Uchiyama, Nanase ;

Hayashi, Tamio .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :25-34

[52] Platinum-catalyzed cross-dehydrogenative coupling reaction in the absence of oxidant [J].

Shu, Xing-Zhong ;

Yang, Yan-Fang ;

Xia, Xiao-Feng ;

Ji, Ke-Gong ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (18) :4077-4079

[53] The second evolution of ionic liquids: From solvents and separations to advanced materials-energetic examples from the ionic liquid cookbook [J].

Smiglak, Marcin ;

Metlen, Andreas ;

Rogers, Robin D. .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (11) :1182-1192

[54] FeCl3-Catalyzed Cascade Cyclization in One Pot: Synthesis of Ring-Fused Tetrahydroquinoline Derivatives from Arylamines and N-Substituted Lactams [J].

Sun, Manman ;

Zhang, Tianshui ;

Bao, Weiliang .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) :8155-8160

[55] Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ [J].

Tsang, Althea S. -K. ;

Todd, Matthew H. .

TETRAHEDRON LETTERS, 2009, 50 (11) :1199-1202

[56] Diastereoselective tetrahydropyrone synthesis through transition-metal-free oxidative carbon-hydrogen bond activation [J].

Tu, Wangyang ;

Liu, Lei ;

Floreancig, Paul E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4184-4187

[57] Chemoselective C-H Bond Activation: Ligand and Solvent Free Iron-Catalyzed Oxidative C-C Cross-Coupling of Tertiary Amines with Terminal, Alkynes. Reaction Scope and Mechanism [J].

Volla, Chandra M. Rao ;

Vogel, Pierre .

ORGANIC LETTERS, 2009, 11 (08) :1701-1704

[58] Copper-Catalyzed Aerobic Oxidative C?H Functionalizations: Trends and Mechanistic Insights [J].

Wendlandt, Alison E. ;

Suess, Alison M. ;

Stahl, Shannon S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11062-11087

[59] Surveying Sterically Demanding N-Heterocyclic Carbene Ligands with Restricted Flexibility for Palladium-catalyzed Cross-Coupling Reactions [J].

Wuertz, Sebastian ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1523-1533

[60] Synthetic applications of photoredox catalysis with visible light [J].

Xi, Yumeng ;

Yi, Hong ;

Lei, Aiwen .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (15) :2387-2403

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